Insecticidal compounds

ABSTRACT

The present invention relates to novel triazole derivatives of formula (I) having insecticidal activity, to processes and intermediates for preparing them, to insecticidal, acaricidal, nematicidal or molluscicidal compositions comprising them and to methods of using them to combat and control insect, acarine, nematode or mollusc pests 
     
       
         
         
             
             
         
       
         
         
           
             wherein R 1 , R 2 , G 1 , G 2 , Q 1  and Q 2  are as defined in claim  1 ; or salts thereof.

This application is a divisional filing of U.S. application Ser. No.14/782,030, filed 2 Oct. 2015, which is a U.S. 371 of InternationalApplication No. PCT/EP2014/056517, filed 1 Apr. 2014, which claimspriority to European Patent Application No. 13161997.5, filed 2 Apr.2013, the contents of all of which are incorporated herein by referenceherein.

The present invention relates to bis-amide derivatives, to processes andintermediates for preparing them, to methods of using them to controlinsect, acarine, nematode and mollusc pests, and to insecticidal,acaricidal, nematicidal and molluscicidal compositions comprising them.

Compounds having insecticidal properties are disclosed in EP1714958,JP2006306771, WO2006137376, EP1916236, WO2007017075, WO2008000438,WO2008/074427, WO2009049845 and WO2010127928. There exists a need foralternative methods of control of pests. Preferably, new compounds maypossess improved insecticidal properties, such as improved efficacy,improved selectivity, reduced toxicity, lower tendency to generateresistance or activity against a broader range of pests. Compounds maybe more advantageously formulated or provide more efficient delivery andretention at sites of action, or may be more readily biodegradable.

It has surprisingly been found that certain bisamide derivatives, whichare substituted by an arylperfluoroalkyl group and a 4-pyridyl or1-oxidopyridin-1-ium-4-yl group, have beneficial properties, which makesthem particularly suitable for use as insecticides.

The present invention therefore provides a compound of formula (I)

whereinQ¹ is 4-pyridyl or 1-oxidopyridin-1-ium-4-yl;Q² is a moiety of formula (II)

whereinY¹ is selected from Cl, Br, I, methyl, ethyl, cyclopropyl, methoxy,difluoromethoxy, trifluoromethoxy, or methoxymethylY⁵ is selected from Cl, Br, I, methyl, ethylY³ is heptafluoroprop-2-yl or nonafluorobut-2-ylX is hydrogen or FR¹ is selected from C₁-C₈alkyl, C₂-C₈alkenyl, C₂-C₈alkynyl,C₁-C₈alkylcarbonyl, C₁-C₈alkoxycarbonyl, hydroxyl, and C₁-C₈alkyloxy;R² is selected from hydrogen, C₁-C₈alkyl, C₂-C₈alkenyl, C₂-C₈alkynyl,C₁-C₈alkylcarbonyl, C₁-C₈alkoxycarbonyl, hydroxyl, C₁-C₈alkyloxy, andaminocarbonyl-C₁-C₄alkylene; andG¹ and G² are both oxygen;or an agrochemically acceptable salt thereof.

The compounds of formula (I) may exist in different geometric or opticalisomers (enantiomers and/or diasteroisomers) or tautomeric forms. Thisinvention covers all such isomers and tautomers and mixtures thereof inall proportions as well as isotopic forms such as deuterated compounds.

Each alkyl moiety either alone or as part of a larger group (such asalkoxy, alkoxycarbonyl, alkylcarbonyl, alkylaminocarbonyl,dialkylaminocarbonyl) is a straight or branched chain and is, forexample, methyl, ethyl, n-propyl, n-butyl, iso-propyl, n-butyl,sec-butyl, iso-butyl or tert-butyl. The alkyl groups are preferably C₁to C₆ alkyl groups, more preferably C₁-C₄ and most preferably C₁-C₃alkyl groups.

Preferably the present invention provides a compound of formula (I)wherein

Q¹ is 4-pyridyl or 1-oxidopyridin-1-ium-4-yl;

Y¹ is selected from Cl, Br, I, methyl, ethyl, methoxy, difluoromethoxy,trifluoromethoxy, or methoxymethyl

Y⁵ is selected from Cl, Br, I, ethyl

Y³ is heptafluoroprop-2-yl or nonafluorobut-2-yl

X is hydrogen or F

R¹ is selected from C₁-C₈alkyl, C₂-C₈alkenyl;

R² is selected from hydrogen, C₁-C₈alkyl, C₂-C₈alkenyl; and

G¹ and G² are both oxygen;

More preferably the present invention provides a compound of formula (I)wherein

Q¹ is 4-pyridyl or 1-oxidopyridin-1-ium-4-yl;

Y¹ is selected from Cl, Br, I, methyl, ethyl;

Y⁵ is selected from Cl, Br, I, ethyl;

Y³ is heptafluoroprop-2-yl

X is hydrogen or F

R¹ is selected from C₂-C₄alkyl;

R² is selected from hydrogen, C₁-C₄alkyl; and

G¹ and G² are both oxygen;

Even more preferably the present invention provides a compound offormula (I) wherein

Q¹ is 4-pyridyl or 1-oxidopyridin-1-ium-4-yl;

Y¹ is selected from Cl, Br, methyl, ethyl;

Y⁵ is selected from Cl, Br, ethyl;

Y³ is heptafluoroprop-2-yl

X is hydrogen or F

R¹ is selected from C₂-C₄alkyl;

R² is selected from hydrogen, C₁-C₄alkyl; and

G¹ and G² are both oxygen;

Most preferably the present invention provides a compound of formula (I)wherein

Q¹ is 4-pyridyl or 1-oxidopyridin-1-ium-4-yl;

Y¹ is selected from Cl, Br, methyl, ethyl;

Y⁵ is selected from Cl, Br, ethyl;

Y³ is heptafluoroprop-2-yl

X is F

R¹ is ethyl;

R² is selected from hydrogen, methyl, ethyl; and

G¹ and G² are both oxygen;

Further preferred values of R¹, R², Y¹ and Y⁵ are, in any combination,as set out below for the different embodiments of the present inventionand G¹ and G² are both oxygen, Q¹ is 4-pyridyl or1-oxidopyridin-1-ium-4-yl; Q² is a moiety of formula (II)

and Y³ is heptafluoroprop-2-yl or nonafluorobut-2-yl.Preferably Y¹ is selected from Cl, Br, I, methyl, ethyl;More preferably Y¹ is selected from Cl, Br, ethyl;Even more preferably Y¹ is selected from Cl, Br;Preferably Y⁵ is selected from Cl, Br, I, ethyl;More preferably Y⁵ is selected from Cl, Br, ethyl;Even more preferably Y⁵ is selected from Cl, Br;Preferably R¹ is selected from methyl, ethyl, propyl, isopropyl, allyl:More preferably R¹ is selected from methyl, ethyl;Even more preferably R¹ is ethyl;Preferably R² is selected from hydrogen, methyl, ethyl, propyl,isopropyl, allyl, aminocarbonyl-ethylene;More preferably R² is selected from hydrogen, methyl, ethyl;Even more preferably R² is hydrogen;

In one embodiment (A) the present invention provides a compound offormula (I) wherein

Q¹ is 4-pyridyl or 1-oxidopyridin-1-ium-4-yl;Q² is a moiety of formula (II)

Y¹ is selected from Cl, Br, I, methyl, ethyl;Y⁵ is selected from Cl, Br, I, ethyl;Y³ is heptafluoroprop-2-yl or nonafluorobut-2-ylX is hydrogen or FR¹ is selected from methyl, ethyl, propyl, isopropyl, allyl;R² is selected from hydrogen, methyl, ethyl, propyl, isopropyl,aminocarbonyl-ethylene; andG¹ and G² are both oxygen;or an agrochemically acceptable salt thereof.

In one preferred embodiment (A) the present invention provides acompound of formula (I) wherein

Y¹ is selected from Cl, Br, methyl, ethyl;

Y⁵ is selected from Cl, Br, ethyl;

Y³ is heptafluoroprop-2-yl

X is hydrogen or F

R¹ is selected from methyl, ethyl;

R² is selected from hydrogen, methyl, ethyl; and

G¹ and G² are both oxygen;

and the other substituents have the meaning as set forth in one of theembodiments (A) above.

More preferably the substituents in the embodiment (A) are as follows

Y¹ is selected from Cl, Br, methyl;

Y⁵ is selected from Cl, Br, ethyl;

Y³ is heptafluoroprop-2-yl

X is hydrogen or F

R¹ is selected from methyl, ethyl;

R² is selected from hydrogen, methyl, ethyl; and

G¹ and G² are both oxygen;

and the other substituents have the meaning as set forth in one of theembodiments (A) above.

Even more preferably the substituents in the embodiment (A) are asfollows

Y¹ is selected from Cl, Br;

Y⁵ is selected from Cl, Br;

Y³ is heptafluoroprop-2-yl

X is hydrogen or F

R¹ is selected from methyl, ethyl, preferably ethyl;

R² is selected from hydrogen, methyl, ethyl; and

G¹ and G² are both oxygen;

and the other substituents have the meaning as set forth in one of theembodiments (A) above.

Most preferably the substituents in the embodiment (A) are as follows

Y¹ is Cl;

Y⁵ is Br;

Y³ is heptafluoroprop-2-yl

X is F

R¹ is selected from methyl, ethyl;

R² is hydrogen; and

G¹ and G² are both oxygen;

and the other substituents have the meaning as set forth in one of theembodiments (A) above.

In one embodiment (B) the present invention provides a compound offormula (I) wherein

Q¹ is 4-pyridyl or 1-oxidopyridin-1-ium-4-yl;Q² is a moiety of formula (II)

Y¹ is selected from Cl, Br, I, methyl, ethyl;Y⁵ is selected from Cl, Br, I, ethyl;Y³ is heptafluoroprop-2-yl or nonafluorobut-2-ylX is hydrogen or FR¹ is selected from ethyl, propyl, isopropyl, allyl;R² is selected from hydrogen, methyl, ethyl, propyl, isopropyl,aminocarbonyl-ethylene; andG¹ and G² are both oxygen;or an agrochemically acceptable salt thereof.

In one preferred embodiment (B) the present invention provides acompound of formula (I) wherein

Y¹ is selected from Cl, Br, methyl, ethyl;

Y⁵ is selected from Cl, Br, ethyl;

Y³ is heptafluoroprop-2-yl or nonafluorobut-2-yl

X is hydrogen or F

R¹ is ethyl;

R² is selected from hydrogen, methyl, ethyl; and

G¹ and G² are both oxygen;

and the other substituents have the meaning as set forth in one of theembodiments (B) above.

More preferably the substituents in the embodiment (B) are as follows

Y¹ is selected from Cl, Br, methyl;

Y⁵ is selected from Cl, Br, ethyl;

Y³ is heptafluoroprop-2-yl

X is hydrogen or F

R¹ is ethyl;

R² is selected from hydrogen, methyl, ethyl; and

G¹ and G² are both oxygen;

and the other substituents have the meaning as set forth in one of theembodiments (B) above.

Even more preferably the substituents in the embodiment (B) are asfollows

Y¹ is Cl;

Y⁵ is Br;

Y³ is heptafluoroprop-2-yl

X is F

R¹ is ethyl;

R² is hydrogen; and

G¹ and G² are both oxygen;

and the other substituents have the meaning as set forth in one of theembodiments (B) above.

The present invention further relates to compounds according to theformula (V)

whereinR is selected from OH, C₁-C₆alkoxy, F, Cl or Br;Q¹ is 4-pyridyl or 1-oxidopyridin-1-ium-4-yl;and the values of X and R¹ as set out above for the differentembodiments of the present invention,or a salt thereof.

The present invention further relates to a process for the production ofcompounds according to the formula (I) or an agrochemically acceptablesalt thereof characterized in that a compound according to the formula(V)

whereinR is selected from OH, C₁-C₆alkoxy, Cl, F or Brand the values of X and R¹ as set out above for the differentembodiments of the present inventionand Q¹ is 4-pyridyl or 1-oxidopyridin-1-ium-4-ylis reacted with and with an amine of formula NHR²Q²whereinQ² is a moiety of formula (II)

and Y³ is heptafluoroprop-2-yl or nonafluorobut-2-ylR², Y¹ and Y⁵ are, in any combination, as set out above for thedifferent embodiments of the present invention.

The present invention further relates to the method of use of compoundsaccording to the formula (V)

for the production of compounds according to formula (III)

whereinX is hydrogen or F,R is selected from OH, C₁-C₆alkoxy, Cl, F or Brand the values of Q¹, Q², R¹, R², Y¹ and Y⁵ as set out above for thedifferent embodiments of the present invention or a salt thereof.

The present invention further relates to compounds according to theformula (IV)

Wherein X is hydrogen or F and R¹ is selected from methyl, ethyl,n-propyl and n-butyl preferably n-butyl,R is selected from hydroxyl, halogen, C₁-C₆-alkyl-C(O)O—, phenyl-C(O)O—,C₁-C₆-alkoxy-C(O)O—, phenoxy-C(O)O—, benzyloxy-C(O)O— and imidazol-1-ylpreferably OH, C₁-C₆alkoxy, Cl, F or Br, more preferably C₁-C₆alkoxy,or a salt thereof.

Thus the present invention relates to compounds according to the formula(IV-a), (IV-b), (IV-c) and (IV-d)

The present invention further relates to the method of use of compoundsaccording to the formula (IV)

for the production of compounds according to formula (V)

wherein X and R¹ has the meaning as set out above for the differentembodiments of the present invention and preferably R¹ is selected frommethyl, ethyl, n-propyl and n-butyl,R is selected from hydroxyl, halogen, C₁-C₆-alkyl-C(O)O—, phenyl-C(O)O—,C₁-C₆-alkoxy-C(O)O—, phenoxy-C(O)O—, benzyloxy-C(O)O— and imidazol-1-ylpreferably OH, C₁-C₆alkoxy, Cl, F or Br, more preferably C₁-C₆alkoxy,and Q¹ is 4-pyridyl or 1-oxidopyridin-1-ium-4-yl;or a salt thereof.

The compounds in Tables 1 to 4 below and in the examples illustrate thecompounds of the invention, but do not limit, the invention.

The compounds of the invention can be distinguished from known compoundsby virtue of greater efficacy at low application rates, which can beverified by the person skilled in the art using the experimentalprocedures outlined in the Examples, using lower application rates ifnecessary, for example 50 ppm, 12.5 ppm, 6 ppm, 3 ppm, 1.5 ppm or 0.8ppm.

TABLE 1 Table 1 provides 112 compounds of formula (III) wherein Q¹ is4-pyridyl, and Q², R¹ and R² have the values listed in the table below.(III)

Compound numbers X R¹ R² Q² 1.1 F Methyl H 2-ethyl-6-bromo-4-(heptafluoroprop-2-yl)phenyl 1.2 F Methyl H 2-ethyl-6-chloro-4-(heptafluoroprop-2-yl)phenyl 1.3 F Methyl H 2-ethyl-6-methyl-4-(heptafluoroprop-2-yl)phenyl 1.4 F Methyl H 2-bromo-6-chloro-4-(heptafluoroprop-2-yl)phenyl 1.5 F Methyl H 2,6-dichloro-4-(heptafluoroprop-2-yl)phenyl 1.6 F Methyl H 2,6-dibromo-4-(heptafluoroprop-2-yl)phenyl 1.7 F Methyl H2,6-diiodo-4-(heptafluoroprop- 2-yl)phenyl 1.8 F Methyl H2-chloro-6-methyl-4- (heptafluoroprop-2-yl)phenyl 1.9 F Methyl H2-chloro-6-methoxymethyl-4- (heptafluoroprop-2-yl)phenyl 1.10 F Methyl H2-bromo-6-methyl-4- (heptafluoroprop-2-yl)phenyl 1.11 F Methyl H2-bromo-6-methoxymethyl-4- (heptafluoroprop-2-yl)phenyl 1.12 F Methyl H2-methyl-6-methoxymethyl-4- (heptafluoroprop-2-yl)phenyl 1.13 F Methyl H2-chloro-6-trifluoromethoxy-4- (heptafluoroprop-2-yl)phenyl 1.14 FMethyl H 2-bromo-6-trifluoromethoxy-4- (heptafluoroprop-2-yl)phenyl 1.15F Ethyl H 2-ethyl-6-bromo-4- (heptafluoroprop-2-yl)phenyl 1.16 F Ethyl H2-ethyl-6-chloro-4- (heptafluoroprop-2-yl)phenyl 1.17 F Ethyl H2-ethyl-6-methyl-4- (heptafluoroprop-2-yl)phenyl 1.18 F Ethyl H2-bromo-6-chloro-4- (heptafluoroprop-2-yl)phenyl 1.19 F Ethyl H2,6-dichloro-4- (heptafluoroprop-2-yl)phenyl 1.20 F Ethyl H2,6-dibromo-4- (heptafluoroprop-2-yl)phenyl 1.21 F Ethyl H2,6-diiodo-4-(heptafluoroprop- 2-yl)phenyl 1.22 F Ethyl H2-chloro-6-methyl-4- (heptafluoroprop-2-yl)phenyl 1.23 F Ethyl H2-chloro-6-methoxymethyl-4- (heptafluoroprop-2-yl)phenyl 1.24 F Ethyl H2-bromo-6-methyl-4- (heptafluoroprop-2-yl)phenyl 1.25 F Ethyl H2-bromo-6-methoxymethyl-4- (heptafluoroprop-2-yl)phenyl 1.26 F Ethyl H2-methyl-6-methoxymethyl-4- (heptafluoroprop-2-yl)phenyl 1.27 F Ethyl H2-chloro-6-trifluoromethoxy-4- (heptafluoroprop-2-yl)phenyl 1.28 F EthylH 2-bromo-6-trifluoromethoxy-4- (heptafluoroprop-2-yl)phenyl 1.29 Fn-Propyl H 2-ethyl-6-bromo-4- (heptafluoroprop-2-yl)phenyl 1.30 Fn-Propyl H 2-ethyl-6-chloro-4- (heptafluoroprop-2-yl)phenyl 1.31 Fn-Propyl H 2-ethyl-6-methyl-4- (heptafluoroprop-2-yl)phenyl 1.32 Fn-Propyl H 2-bromo-6-chloro-4- (heptafluoroprop-2-yl)phenyl 1.33 Fn-Propyl H 2,6-dichloro-4- (heptafluoroprop-2-yl)phenyl 1.34 F n-PropylH 2,6-dibromo-4- (heptafluoroprop-2-yl)phenyl 1.35 F n-Propyl H2,6-diiodo-4-(heptafluoroprop- 2-yl)phenyl 1.36 F n-Propyl H2-chloro-6-methyl-4- (heptafluoroprop-2-yl)phenyl 1.37 F n-Propyl H2-chloro-6-methoxymethyl-4- (heptafluoroprop-2-yl)phenyl 1.38 F n-PropylH 2-bromo-6-methyl-4- (heptafluoroprop-2-yl)phenyl 1.39 F n-Propyl H2-bromo-6-methoxymethyl-4- (heptafluoroprop-2-yl)phenyl 1.40 F n-PropylH 2-methyl-6-methoxymethyl-4- (heptafluoroprop-2-yl)phenyl 1.41 Fn-Propyl H 2-chloro-6-trifluoromethoxy-4- (heptafluoroprop-2-yl)phenyl1.42 F n-Propyl H 2-bromo-6-trifluoromethoxy-4-(heptafluoroprop-2-yl)phenyl 1.43 F Methyl Methyl 2-ethyl-6-bromo-4-(heptafluoroprop-2-yl)phenyl 1.44 F Methyl Methyl 2-ethyl-6-chloro-4-(heptafluoroprop-2-yl)phenyl 1.45 F Methyl Methyl 2-ethyl-6-methyl-4-(heptafluoroprop-2-yl)phenyl 1.46 F Methyl Methyl 2-bromo-6-chloro-4-(heptafluoroprop-2-yl)phenyl 1.47 F Methyl Methyl 2,6-dichloro-4-(heptafluoroprop-2-yl)phenyl 1.48 F Methyl Methyl 2,6-dibromo-4-(heptafluoroprop-2-yl)phenyl 1.49 F Methyl Methyl2,6-diiodo-4-(heptafluoroprop- 2-yl)phenyl 1.50 F Methyl Methyl2-chloro-6-methyl-4- (heptafluoroprop-2-yl)phenyl 1.51 F Methyl Methyl2-chloro-6-methoxymethyl-4- (heptafluoroprop-2-yl)phenyl 1.52 F MethylMethyl 2-bromo-6-methyl-4- (heptafluoroprop-2-yl)phenyl 1.53 F MethylMethyl 2-bromo-6-methoxymethyl-4- (heptafluoroprop-2-yl)phenyl 1.54 FMethyl Methyl 2-methyl-6-methoxymethyl-4- (heptafluoroprop-2-yl)phenyl1.55 F Methyl Methyl 2-chloro-6-trifluoromethoxy-4-(heptafluoroprop-2-yl)phenyl 1.56 F Methyl Methyl2-bromo-6-trifluoromethoxy-4- (heptafluoroprop-2-yl)phenyl 1.57 H MethylH 2-ethyl-6-bromo-4- (heptafluoroprop-2-yl)phenyl 1.58 H Methyl H2-ethyl-6-chloro-4- (heptafluoroprop-2-yl)phenyl 1.59 H Methyl H2-ethyl-6-methyl-4- (heptafluoroprop-2-yl)phenyl 1.60 H Methyl H2-bromo-6-chloro-4- (heptafluoroprop-2-yl)phenyl 1.61 H Methyl H2,6-dichloro-4- (heptafluoroprop-2-yl)phenyl 1.62 H Methyl H2,6-dibromo-4- (heptafluoroprop-2-yl)phenyl 1.63 H Methyl H2,6-diiodo-4-(heptafluoroprop- 2-yl)phenyl 1.64 H Methyl H2-chloro-6-methyl-4- (heptafluoroprop-2-yl)phenyl 1.65 H Methyl H2-chloro-6-methoxymethyl-4- (heptafluoroprop-2-yl)phenyl 1.66 H Methyl H2-bromo-6-methyl-4- (heptafluoroprop-2-yl)phenyl 1.67 H Methyl H 2bromo-6-methoxymethyl-4- (heptafluoroprop-2-yl)phenyl 1.68 H Methyl H 2methyl-6-methoxymethyl-4- (heptafluoroprop-2-yl)phenyl 1.69 H Methyl H 2chloro-6-trifluoromethoxy-4- (heptafluoroprop-2-yl)phenyl 1.70 H MethylH 2 bromo-6-trifluoromethoxy-4- (heptafluoroprop-2-yl)phenyl 1.71 HEthyl H 2-ethyl-6-bromo-4- (heptafluoroprop-2-yl)phenyl 1.72 H Ethyl H2-ethyl-6-chloro-4- (heptafluoroprop-2-yl)phenyl 1.73 H Ethyl H2-ethyl-6-methyl-4- (heptafluoroprop-2-yl)phenyl 1.74 H Ethyl H2-bromo-6-chloro-4- (heptafluoroprop-2-yl)phenyl 1.75 H Ethyl H2,6-dichloro-4- (heptafluoroprop-2-yl)phenyl 1.76 H Ethyl H2,6-dibromo-4- (heptafluoroprop-2-yl)phenyl 1.77 H Ethyl H2,6-diiodo-4-(heptafluoroprop- 2-yl)phenyl 1.78 H Ethyl H2-chloro-6-methyl-4- (heptafluoroprop-2-yl)phenyl 1.79 H Ethyl H2-chloro-6-methoxymethyl-4- (heptafluoroprop-2-yl)phenyl 1.80 H Ethyl H2-bromo-6-methyl-4- (heptafluoroprop-2-yl)phenyl 1.81 H Ethyl H 2bromo-6-methoxymethyl-4- (heptafluoroprop-2-yl)phenyl 1.82 H Ethyl H 2methyl-6-methoxymethyl-4- (heptafluoroprop-2-yl)phenyl 1.83 H Ethyl H 2chloro-6-trifluoromethoxy-4- (heptafluoroprop-2-yl)phenyl 1.84 H Ethyl H2 bromo-6-trifluoromethoxy-4- (heptafluoroprop-2-yl)phenyl 1.85 Hn-Propyl H 2-ethyl-6-bromo-4- (heptafluoroprop-2-yl)phenyl 1.86 Hn-Propyl H 2-ethyl-6-chloro-4- (heptafluoroprop-2-yl)phenyl 1.87 Hn-Propyl H 2-ethyl-6-methyl-4- (heptafluoroprop-2-yl)phenyl 1.88 Hn-Propyl H 2-bromo-6-chloro-4- (heptafluoroprop-2-yl)phenyl 1.89 Hn-Propyl H 2,6-dichloro-4- (heptafluoroprop-2-yl)phenyl 1.90 H n-PropylH 2,6-dibromo-4- (heptafluoroprop-2-yl)phenyl 1.91 H n-Propyl H2,6-diiodo-4-(heptafluoroprop- 2-yl)phenyl 1.92 H n-Propyl H2-chloro-6-methyl-4- (heptafluoroprop-2-yl)phenyl 1.93 H n-Propyl H2-chloro-6-methoxymethyl-4- (heptafluoroprop-2-yl)phenyl 1.94 H n-PropylH 2-bromo-6-methyl-4- (heptafluoroprop-2-yl)phenyl 1.95 H n-Propyl H 2bromo-6-methoxymethyl-4- (heptafluoroprop-2-yl)phenyl 1.96 H n-Propyl H2 methyl-6-methoxymethyl-4- (heptafluoroprop-2-yl)phenyl 1.97 H n-PropylH 2 chloro-6-trifluoromethoxy-4- (heptafluoroprop-2-yl)phenyl 1.98 Hn-Propyl H 2 bromo-6-trifluoromethoxy-4- (heptafluoroprop-2-yl)phenyl1.99 H Methyl Methyl 2-ethyl-6-bromo-4- (heptafluoroprop-2-yl)phenyl1.100 H Methyl Methyl 2-ethyl-6-chloro-4- (heptafluoroprop-2-yl)phenyl1.101 H Methyl Methyl 2-ethyl-6-methyl-4- (heptafluoroprop-2-yl)phenyl1.102 H Methyl Methyl 2-bromo-6-chloro-4- (heptafluoroprop-2-yl)phenyl1.103 H Methyl Methyl 2,6-dichloro-4- (heptafluoroprop-2-yl)phenyl 1.104H Methyl Methyl 2,6-dibromo-4- (heptafluoroprop-2-yl)phenyl 1.105 HMethyl Methyl 2,6-diiodo-4-(heptafluoroprop- 2-yl)phenyl 1.106 H MethylMethyl 2-chloro-6-methyl-4- (heptafluoroprop-2-yl)phenyl 1.107 H MethylMethyl 2-chloro-6-methoxymethyl-4- (heptafluoroprop-2-yl)phenyl 1.108 HMethyl Methyl 2-bromo-6-methyl-4- (heptafluoroprop-2-yl)phenyl 1.109 HMethyl Methyl 2 bromo-6-methoxymethyl-4- (heptafluoroprop-2-yl)phenyl1.110 H Methyl Methyl 2 methyl-6-methoxymethyl-4-(heptafluoroprop-2-yl)phenyl 1.111 H Methyl Methyl 2chloro-6-trifluoromethoxy-4- (heptafluoroprop-2-yl)phenyl 1.112 H MethylMethyl 2 bromo-6-trifluoromethoxy-4- (heptafluoroprop-2-yl)phenyl

TABLE 2 Table 2 provides 112 compounds of formula (III) wherein Q¹ is1-oxidopyridin-1-ium-4-yl, and Q², R¹ and R² have the values listed inthe table below. (III)

Compound numbers X R¹ R² Q² 2.1 F Methyl H 2-ethyl-6-bromo-4-(heptafluoroprop-2-yl)phenyl 2.2 F Methyl H 2-ethyl-6-chloro-4-(heptafluoroprop-2-yl)phenyl 2.3 F Methyl H 2-ethyl-6-methyl-4-(heptafluoroprop-2-yl)phenyl 2.4 F Methyl H 2-bromo-6-chloro-4-(heptafluoroprop-2-yl)phenyl 2.5 F Methyl H 2,6-dichloro-4-(heptafluoroprop-2-yl)phenyl 2.6 F Methyl H 2,6-dibromo-4-(heptafluoroprop-2-yl)phenyl 2.7 F Methyl H2,6-diiodo-4-(heptafluoroprop- 2-yl)phenyl 2.8 F Methyl H2-chloro-6-methyl-4- (heptafluoroprop-2-yl)phenyl 2.9 F Methyl H2-chloro-6-methoxymethyl-4- (heptafluoroprop-2-yl)phenyl 2.10 F Methyl H2-bromo-6-methyl-4- (heptafluoroprop-2-yl)phenyl 2.11 F Methyl H2-bromo-6-methoxymethyl-4- (heptafluoroprop-2-yl)phenyl 2.12 F Methyl H2-methyl-6-methoxymethyl-4- (heptafluoroprop-2-yl)phenyl 2.13 F Methyl H2-chloro-6-trifluoromethoxy-4- (heptafluoroprop-2-yl)phenyl 2.14 FMethyl H 2-bromo-6-trifluoromethoxy-4- (heptafluoroprop-2-yl)phenyl 2.15F Ethyl H 2-ethyl-6-bromo-4- (heptafluoroprop-2-yl)phenyl 2.16 F Ethyl H2-ethyl-6-chloro-4- (heptafluoroprop-2-yl)phenyl 2.17 F Ethyl H2-ethyl-6-methyl-4- (heptafluoroprop-2-yl)phenyl 2.18 F Ethyl H2-bromo-6-chloro-4- (heptafluoroprop-2-yl)phenyl 2.19 F Ethyl H2,6-dichloro-4- (heptafluoroprop-2-yl)phenyl 2.20 F Ethyl H2,6-dibromo-4- (heptafluoroprop-2-yl)phenyl 2.21 F Ethyl H2,6-diiodo-4-(heptafluoroprop- 2-yl)phenyl 2.22 F Ethyl H2-chloro-6-methyl-4- (heptafluoroprop-2-yl)phenyl 2.23 F Ethyl H2-chloro-6-methoxymethyl-4- (heptafluoroprop-2-yl)phenyl 2.24 F Ethyl H2-bromo-6-methyl-4- (heptafluoroprop-2-yl)phenyl 2.25 F Ethyl H2-bromo-6-methoxymethyl-4- (heptafluoroprop-2-yl)phenyl 2.26 F Ethyl H2-methyl-6-methoxymethyl-4- (heptafluoroprop-2-yl)phenyl 2.27 F Ethyl H2-chloro-6-trifluoromethoxy-4- (heptafluoroprop-2-yl)phenyl 2.28 F EthylH 2-bromo-6-trifluoromethoxy-4- (heptafluoroprop-2-yl)phenyl 2.29 Fn-Propyl H 2-ethyl-6-bromo-4- (heptafluoroprop-2-yl)phenyl 2.30 Fn-Propyl H 2-ethyl-6-chloro-4- (heptafluoroprop-2-yl)phenyl 2.31 Fn-Propyl H 2-ethyl-6-methyl-4- (heptafluoroprop-2-yl)phenyl 2.32 Fn-Propyl H 2-bromo-6-chloro-4- (heptafluoroprop-2-yl)phenyl 2.33 Fn-Propyl H 2,6-dichloro-4- (heptafluoroprop-2-yl)phenyl 2.34 F n-PropylH 2,6-dibromo-4- (heptafluoroprop-2-yl)phenyl 2.35 F n-Propyl H2,6-diiodo-4-(heptafluoroprop- 2-yl)phenyl 2.36 F n-Propyl H2-chloro-6-methyl-4- (heptafluoroprop-2-yl)phenyl 2.37 F n-Propyl H2-chloro-6-methoxymethyl-4- (heptafluoroprop-2-yl)phenyl 2.38 F n-PropylH 2-bromo-6-methyl-4- (heptafluoroprop-2-yl)phenyl 2.39 F n-Propyl H2-bromo-6-methoxymethyl-4- (heptafluoroprop-2-yl)phenyl 2.40 F n-PropylH 2-methyl-6-methoxymethyl-4- (heptafluoroprop-2-yl)phenyl 2.41 Fn-Propyl H 2-chloro-6-trifluoromethoxy-4- (heptafluoroprop-2-yl)phenyl2.42 F n-Propyl H 2-bromo-6-trifluoromethoxy-4-(heptafluoroprop-2-yl)phenyl 2.43 F Methyl Methyl 2-ethyl-6-bromo-4-(heptafluoroprop-2-yl)phenyl 2.44 F Methyl Methyl 2-ethyl-6-chloro-4-(heptafluoroprop-2-yl)phenyl 2.45 F Methyl Methyl 2-ethyl-6-methyl-4-(heptafluoroprop-2-yl)phenyl 2.46 F Methyl Methyl 2-bromo-6-chloro-4-(heptafluoroprop-2-yl)phenyl 2.47 F Methyl Methyl 2,6-dichloro-4-(heptafluoroprop-2-yl)phenyl 2.48 F Methyl Methyl 2,6-dibromo-4-(heptafluoroprop-2-yl)phenyl 2.49 F Methyl Methyl2,6-diiodo-4-(heptafluoroprop- 2-yl)phenyl 2.50 F Methyl Methyl2-chloro-6-methyl-4- (heptafluoroprop-2-yl)phenyl 2.51 F Methyl Methyl2-chloro-6-methoxymethyl-4- (heptafluoroprop-2-yl)phenyl 2.52 F MethylMethyl 2-bromo-6-methyl-4- (heptafluoroprop-2-yl)phenyl 2.53 F MethylMethyl 2-bromo-6-methoxymethyl-4- (heptafluoroprop-2-yl)phenyl 2.54 FMethyl Methyl 2-methyl-6-methoxymethyl-4- (heptafluoroprop-2-yl)phenyl2.55 F Methyl Methyl 2-chloro-6-trifluoromethoxy-4-(heptafluoroprop-2-yl)phenyl 2.56 F Methyl Methyl2-bromo-6-trifluoromethoxy-4- (heptafluoroprop-2-yl)phenyl 2.57 H MethylH 2-ethyl-6-bromo-4- (heptafluoroprop-2-yl)phenyl 2.58 H Methyl H2-ethyl-6-chloro-4- (heptafluoroprop-2-yl)phenyl 2.59 H Methyl H2-ethyl-6-methyl-4- (heptafluoroprop-2-yl)phenyl 2.60 H Methyl H2-bromo-6-chloro-4- (heptafluoroprop-2-yl)phenyl 2.61 H Methyl H2,6-dichloro-4- (heptafluoroprop-2-yl)phenyl 2.62 H Methyl H2,6-dibromo-4- (heptafluoroprop-2-yl)phenyl 2.63 H Methyl H2,6-diiodo-4-(heptafluoroprop- 2-yl)phenyl 2.64 H Methyl H2-chloro-6-methyl-4- (heptafluoroprop-2-yl)phenyl 2.65 H Methyl H2-chloro-6-methoxymethyl-4- (heptafluoroprop-2-yl)phenyl 2.66 H Methyl H2-bromo-6-methyl-4- (heptafluoroprop-2-yl)phenyl 2.67 H Methyl H2-bromo-6-methoxymethyl-4- (heptafluoroprop-2-yl)phenyl 2.68 H Methyl H2-methyl-6-methoxymethyl-4- (heptafluoroprop-2-yl)phenyl 2.69 H Methyl H2-chloro-6-trifluoromethoxy-4- (heptafluoroprop-2-yl)phenyl 2.70 HMethyl H 2-bromo-6-trifluoromethoxy-4- (heptafluoroprop-2-yl)phenyl 2.71H Ethyl H 2-ethyl-6-bromo-4- (heptafluoroprop-2-yl)phenyl 2.72 H Ethyl H2-ethyl-6-chloro-4- (heptafluoroprop-2-yl)phenyl 2.73 H Ethyl H2-ethyl-6-methyl-4- (heptafluoroprop-2-yl)phenyl 2.74 H Ethyl H2-bromo-6-chloro-4- (heptafluoroprop-2-yl)phenyl 2.75 H Ethyl H2,6-dichloro-4- (heptafluoroprop-2-yl)phenyl 2.76 H Ethyl H2,6-dibromo-4- (heptafluoroprop-2-yl)phenyl 2.77 H Ethyl H2,6-diiodo-4-(heptafluoroprop- 2-yl)phenyl 2.78 H Ethyl H2-chloro-6-methyl-4- (heptafluoroprop-2-yl)phenyl 2.79 H Ethyl H2-chloro-6-methoxymethyl-4- (heptafluoroprop-2-yl)phenyl 2.80 H Ethyl H2-bromo-6-methyl-4- (heptafluoroprop-2-yl)phenyl 2.81 H Ethyl H2-bromo-6-methoxymethyl-4- (heptafluoroprop-2-yl)phenyl 2.82 H Ethyl H2-methyl-6-methoxymethyl-4- (heptafluoroprop-2-yl)phenyl 2.83 H Ethyl H2-chloro-6-trifluoromethoxy-4- (heptafluoroprop-2-yl)phenyl 2.84 H EthylH 2-bromo-6-trifluoromethoxy-4- (heptafluoroprop-2-yl)phenyl 2.85 Hn-Propyl H 2-ethyl-6-bromo-4- (heptafluoroprop-2-yl)phenyl 2.86 Hn-Propyl H 2-ethyl-6-chloro-4- (heptafluoroprop-2-yl)phenyl 2.87 Hn-Propyl H 2-ethyl-6-methyl-4- (heptafluoroprop-2-yl)phenyl 2.88 Hn-Propyl H 2-bromo-6-chloro-4- (heptafluoroprop-2-yl)phenyl 2.89 Hn-Propyl H 2,6-dichloro-4- (heptafluoroprop-2-yl)phenyl 2.90 H n-PropylH 2,6-dibromo-4- (heptafluoroprop-2-yl)phenyl 2.91 H n-Propyl H2,6-diiodo-4-(heptafluoroprop- 2-yl)phenyl 2.92 H n-Propyl H2-chloro-6-methyl-4- (heptafluoroprop-2-yl)phenyl 2.93 H n-Propyl H2-chloro-6-methoxymethyl-4- (heptafluoroprop-2-yl)phenyl 2.94 H n-PropylH 2-bromo-6-methyl-4- (heptafluoroprop-2-yl)phenyl 2.95 H n-Propyl H2-bromo-6-methoxymethyl-4- (heptafluoroprop-2-yl)phenyl 2.96 H n-PropylH 2-methyl-6-methoxymethyl-4- (heptafluoroprop-2-yl)phenyl 2.97 Hn-Propyl H 2-chloro-6-trifluoromethoxy-4- (heptafluoroprop-2-yl)phenyl2.98 H n-Propyl H 2-bromo-6-trifluoromethoxy-4-(heptafluoroprop-2-yl)phenyl 2.99 H Methyl Methyl 2-ethyl-6-bromo-4-(heptafluoroprop-2-yl)phenyl 2.100 H Methyl Methyl 2-ethyl-6-chloro-4-(heptafluoroprop-2-yl)phenyl 2.101 H Methyl Methyl 2-ethyl-6-methyl-4-(heptafluoroprop-2-yl)phenyl 2.102 H Methyl Methyl 2-bromo-6-chloro-4-(heptafluoroprop-2-yl)phenyl 2.103 H Methyl Methyl 2,6-dichloro-4-(heptafluoroprop-2-yl)phenyl 2.104 H Methyl Methyl 2,6-dibromo-4-(heptafluoroprop-2-yl)phenyl 2.105 H Methyl Methyl2,6-diiodo-4-(heptafluoroprop- 2-yl)phenyl 2.106 H Methyl Methyl2-chloro-6-methyl-4- (heptafluoroprop-2-yl)phenyl 2.107 H Methyl Methyl2-chloro-6-methoxymethyl-4- (heptafluoroprop-2-yl)phenyl 2.108 H MethylMethyl 2-bromo-6-methyl-4- (heptafluoroprop-2-yl)phenyl 2.109 H MethylMethyl 2-bromo-6-methoxymethyl-4- (heptafluoroprop-2-yl)phenyl 2.110 HMethyl Methyl 2-methyl-6-methoxymethyl-4- (heptafluoroprop-2-yl)phenyl2.111 H Methyl Methyl 2-chloro-6-trifluoromethoxy-4-(heptafluoroprop-2-yl)phenyl 2.112 H Methyl Methyl2-bromo-6-trifluoromethoxy-4- (heptafluoroprop-2-yl)phenyl

TABLE 3 Table 3 provides 30 compounds of formula (V) wherein Q¹ is4-pyridyl, and R¹ and R have the values listed in the table below. Thecompounds 3.1 to 3.3 and 3.16 to 3.18 are not according to theinvention. (V)

Compound numbers X R¹ R 3.1 F H OH 3.2 F H Methoxy 3.3 F H Cl 3.4 FMethyl OH 3.5 F Methyl Methoxy 3.6 F Methyl Cl 3.7 F Ethyl OH 3.8 FEthyl Methoxy 3.9 F Ethyl Cl 3.10 F n-Propyl OH 3.11 F n-Propyl Methoxy3.12 F n-Propyl Cl 3.13 F n-Butyl OH 3.14 F n-Butyl Methoxy 3.15 Fn-Butyl Cl 3.16 H H OH 3.17 H H Methoxy 3.18 H H Cl 3.19 H Methyl OH3.20 H Methyl Methoxy 3.21 H Methyl Cl 3.22 H Ethyl OH 3.23 H EthylMethoxy 3.24 H Ethyl Cl 3.25 H n-Propyl OH 3.26 H n-Propyl Methoxy 3.27H n-Propyl Cl 3.28 H n-Butyl OH 3.29 H n-Butyl Methoxy 3.30 H n-Butyl Cl

TABLE 4 Table 4 provides 30 compounds of formula (V) wherein Q¹ is1-oxidopyridin-1-ium-4-yl, and R¹ and R have the values listed in thetable below. The compounds 4.1 to 4.3 and 4.16 to 4.18 are not accordingto the invention. (V)

Compound numbers X R¹ R 4.1 F H OH 4.2 F H Methoxy 4.3 F H Cl 4.4 FMethyl OH 4.5 F Methyl Methoxy 4.6 F Methyl Cl 4.7 F Ethyl OH 4.8 FEthyl Methoxy 4.9 F Ethyl Cl 4.10 F n-Propyl OH 4.11 F n-Propyl Methoxy4.12 F n-Propyl Cl 4.13 F n-Butyl OH 4.14 F n-Butyl Methoxy 4.15 Fn-Butyl Cl 4.16 H H OH 4.17 H H Methoxy 4.18 H H Cl 4.19 H Methyl OH4.20 H Methyl Methoxy 4.21 H Methyl Cl 4.22 H Ethyl OH 4.23 H EthylMethoxy 4.24 H Ethyl Cl 4.25 H n-Propyl OH 4.26 H n-Propyl Methoxy 4.27H n-Propyl Cl 4.28 H n-Butyl OH 4.29 H n-Butyl Methoxy 4.30 H n-Butyl Cl

The compounds of the invention may be made by a variety of methods, forexample, the methods disclosed in WO 08/000438 or WO 2010/127928.

1) Compounds of formula (III) may be made by treatment of compounds offormula (V), wherein R is OH, C₁-C₆alkoxy, Cl, F or Br with an amine offormula NHR²Q². When R is OH such reactions may be carried out in thepresence of a coupling reagent, such as DCC(N,N′-dicyclohexyl-carbodiimide), EDC(1-ethyl-3-[3-dimethylamino-propyl]carbodiimide hydrochloride) or BOP-Cl(bis(2-oxo-3-oxazolidinyl)phosphonic chloride), in the presence of abase, such as pyridine, triethylamine, 4-(dimethylamino)pyridine ordiisopropylethylamine, and optionally in the presence of a nucleophiliccatalyst, such as hydroxybenzotriazole. When R is Cl, such reactions maybe carried out under basic conditions, for example in the presence ofpyridine, triethylamine, 4-(dimethylamino)pyridine ordiisopropylethylamine, and optionally in the presence of a nucleophiliccatalyst. Alternatively, the reaction may be conducted in a biphasicsystem comprising an organic solvent, preferably ethyl acetate, and anaqueous solvent, preferably a solution of sodium bicarbonate. When R isC₁-C₆alkoxy the ester may be converted directly to the amide by heatingthe ester and amine together in a thermal process.

2) Acid halides of formula (V), wherein R is Cl, F or Br, may be madefrom carboxylic acids of formula (V), wherein R is OH by treatment withthionyl chloride or oxalyl chloride.

3) Carboxylic acids of formula (V), wherein R is OH, may be formed fromesters of formula (V), wherein R is C₁-C₆alkoxy by treatment of theester with an alkali hydroxide, such as sodium hydroxide, in a solvent,such as ethanol.

4) Esters of formula (V), wherein R is C₁-C₆alkoxy, may be made bytreatment of compounds of formula (IV), wherein R is C₁-C₆alkoxy, byacylation with a carboxylic acid of formula Q¹-COOH or an acid halide offormula Q¹-COHal, wherein Hal is Cl, F or Br, under standard conditionsas described in 1).

5) Compounds of formula (IV), wherein R is C₁-C₆alkoxy, may be made fromcompounds of formula (VI) by sequential treatment with an alcohol R—OHunder acidic conditions and then formation of the N—R¹ bond. Forexample, reductive amination may be achieved by treatment of the aminewith an aldehyde or ketone and a reducing agent such as sodiumcyanoborohydride. Alternatively, alkylation may be achieved by treatingthe amine with an alkylating agent such as an alkyl halide, optionallyin the presence of a base. Alternatively, arylation may be achieved bytreatment of the amine with an aryl halide or sulfonate in the presenceof a suitable catalyst/ligand system, often a palladium (0) complex.

6) Alternatively, compounds of formula (IV), wherein R is C₁-C₆alkoxy,may be made from a compound of formula (VII), wherein R is C₁-C₆alkoxyand LG is a leaving group, such as bromo, chloro or sulfonate, via thedisplacement of the leaving group by an amine of formula R¹—NH₂ or otherimine analogue followed by hydrolysis with a metal catalyst. See, forexample: Chemical Communications (2009), (14), 1891-1893 or Journal ofOrganic Chemistry (2000), 65(8), 2612-2614.

Compounds of formula (VII) and amines of formula R¹—NH₂ are either knowncompounds or may be made by methods known to a person skilled in theart.

6a) Alternatively, compounds of formula (IV), wherein R is C₁-C₆alkoxy,may be made from a compounds of formula XV, wherein R is C₁-C₆alkoxy viareduction in the presence of a metal catalyst and a suitable two carbonbuilding block such as acetaldehyde or acetonitrile. See for example: J.Org. Chem. 2007, 72, 9815 or Org. Lett. 2005, 7, 471

7) Alternatively, compounds of formula (III), may be made by thetreatment of compounds of formula (IX) with a carboxylic acid of formulaQ¹-COOH or an acid halide of formula Q¹-COHal, wherein Hal is Cl, F orBr, under standard conditions as described in 1).

8) Compounds of formula (IX) may be formed from compounds of formula(VIII), wherein P is a suitable protecting group and R is OH, Cl orC₁-C₆alkoxy, by amide bond formation with an amine of formula NHR²Q²under standard conditions as described in 1), followed by removal of theprotecting group P* under standard conditions.

9) Compounds of formula (VIII), wherein R is OH or C₁-C₆alkoxy, may bemade by the protection of the amine functionality in compounds offormula (IV), wherein R is OH or C₁-C₆alkoxy. Suitable protecting groupsinclude carbamates (such as tert-butyloxycarbonyl, allyloxycarbonyl andbenzyloxycarbonyl), trialkylsilyl groups (such astert-butyldimethylsilyl) and acyl groups (such as acetyl).

10) For compounds of formula (VIII) and compounds of formula (IV), theesters, wherein R is C₁-C₆alkoxy, may be hydrolysed to the acids,wherein R is OH, by treatment with an alkali hydroxide, such as sodiumhydroxide, in a solvent, such as ethanol. The acids may be converted tothe acid chlorides, wherein R is Cl, by treatment with thionyl chlorideor oxalyl chloride as described in 2) and 3).

11) Alternatively, compounds of formula (IV), wherein R is OH, Cl, F, Bror C₁-C₆alkoxy, may be converted directly to compounds of formula (IX)by amide bond formation with an amine of formula NHR²Q² under standardconditions as described in 1).

12) Alternatively, compounds of formula (IX) may be made from compoundsof formula (XI), wherein LG is a leaving group such as iodo, bromo,chloro or sulfonate, by displacement of the leaving group with acompound of formula R¹—NH₂ or other imine analogue followed byhydrolysis with a metal catalyst. See for example: ChemicalCommunications (2009), (14), 1891-1893 or Journal of Organic Chemistry(2000), 65(8), 2612-2614.

13) Compounds of formula (XI) may be made from compounds of formula (X),wherein R is Cl or OH and LG is a leaving group as described in 12), viaamide bond formation under standard conditions as described in 1).Compounds of formula (X) and formula (IV) are either known compounds ormay be made by methods known to the person skilled in the art.

14) An alternative synthesis of compounds of formula (IX), wherein R¹ ishydrogen, may be achieved by the reduction of nitro compounds of formula(XIII), such as by treatment with tin chloride under acidic conditions,or hydrogenation catalysed by a noble metal such as palladium on carbon.

15) Compounds of formula (XIII) may be derived from compounds of formula(XII), wherein R is OH, Cl, or C₁-C₆alkoxy, via acylation with an amineof formula NHR²Q² under the standard conditions as described in 1).

16) For compounds of formula (XII), the esters, wherein R isC₁-C₆alkoxy, may be hydrolysed to the acids, wherein R is OH, bytreatment with an alkali hydroxide, such as sodium hydroxide, in asolvent, such as ethanol as described in 3). The acids may be convertedto the acid chlorides, wherein R is Cl, by treatment with thionylchloride or oxalyl chloride as described in 2). Compounds of formula(XII) are either known or may be made by methods known to a personskilled in the art.

17) Compounds of formula (XII) can be made from a compound of formula(XIV) wherein LG is a leaving group, such as diazonio or chlorine, byreaction with fluoride, such as KF.

The displacement of a halogen with a fluoride nucleophile can also becarried out on intermediates of formula (XIII).

18) Compounds of formula (XIII) where R² is selected from C₁-C₈alkyl,C₂-C₈alkenyl, C₂-C₈alkynyl, may be prepared from compounds of formula(XIII) where R² is hydrogen, by treating them with a base, followed byan appropriate electrophile. Example of bases can be metal hydrides,like sodium hydride, potassium hydride or calcium hydride or metalalkoxide, like potassium t-butoxide, or organometals, likemethyllithium, butyllithium, alkylmagnesium halide, metal amides likelithium diisopropylamide or lithium hexamethyldisilazide or a basicsalt, like potassium carbonate. A solvent can be used. It could be, forexample, a polar aprotic solvent like DMF or an ether like THF ordimethoxyethane. The reaction can be performed below 0° C. or above 80°C., but preferably in DMF between 0° C. and 25° C. The electrophile isR²—X′ where R² is selected from C₁-C₈alkyl, C₂-C₈alkenyl, C₂-C₈alkynyland X′ is a leaving group like bromide, chloride, iodide, mesylate,triflate, tosylate and the like. The base can be used in excess, as wellas the electrophile, but preferably, the base is used in equivalentamounts as well as the electrophilic reagent.

19) Compounds of formula (III) wherein Q¹ and Q² are as defined in thedescription, R¹ is different from hydrogen and R² is selected fromC₁-C₈alkyl, C₂-C₈alkenyl, C₂-C₈alkynyl, may be prepared from compound offormula (III) wherein Q¹ and Q² are as defined in the description, R¹ isdifferent from hydrogen and R² is hydrogen, by treating it with a base,followed by an appropriate electrophile. Example of bases can be metalhydrides, like sodium hydride, potassium hydride or calcium hydride ormetal alkoxide, like potassium t-butoxide, or organometals, likemethyllithium, butyllithium, alkylmagnesium halide, metal amides likelithium diisopropylamide or lithium hexamethyldisilazide or a basicsalt, like potassium carbonate. A solvent can be used. It could be, forexample, a polar aprotic solvent like DMF or an ether like THF ordimethoxyethane. The reaction can be performed below 0° C. or above 80°C., but preferably in DMF between 0° C. and 25° C. The electrophile isR²—X′ where R² is selected from C₁-C₈alkyl, C₂-C₈alkenyl, C₂-C₈alkynyland X′ is a leaving group like bromide, chloride, iodide, mesylate,triflate, tosylate and the like. The base can be used in excess, as wellas the electrophile, but preferably, the base is used in equivalentamounts as well as the electrophilic reagent. Preferred conditions aresodium hydride in DMF between 0° C. and 25° C.

20) Compounds of formula (III) wherein Q¹ and Q² are as defined in thedescription, R¹ is selected from C₁-C₈alkyl, C₂-C₈alkenyl, C₂-C₈alkynyland R² is different from hydrogen, may be prepared from compound offormula (III) wherein Q¹ and Q² are as defined in the description, R¹ ishydrogen and R² is different from hydrogen, by treating it with a base,followed by an appropriate electrophile. Example of bases can be metalhydrides, like sodium hydride, potassium hydride or calcium hydride ormetal alkoxide, like potassium t-butoxide, or organometals, likemethyllithium, butyllithium, alkylmagnesium halide, metal amides likelithium diisopropylamide or lithium hexamethyldisilazide or a basicsalt, like potassium carbonate. A solvent can be used. It could be, forexample, a polar aprotic solvent like DMF or an ether like THF ordimethoxyethane. The reaction can be performed below 0° C. or above 80°C., but preferably in DMF between 0° C. and 25° C. The electrophile isR¹—X′ where R¹ is selected from C₁-C₈alkyl, C₂-C₈alkenyl, C₂-C₈alkynyland X′ is a leaving group like bromide, chloride, iodide, mesylate,triflate, tosylate and the like. The base can be used in excess, as wellas the electrophile, but preferably, the base is used in equivalentamounts as well as the electrophilic reagent. Preferred conditions aresodium hydride in DMF between 0° C. and 25° C.

The compounds of formula (I) can be used to combat and controlinfestations of insect pests such as Lepidoptera, Diptera, Hemiptera,Thysanoptera, Orthoptera, Dictyoptera, Coleoptera, Siphonaptera,Hymenoptera and Isoptera and also other invertebrate pests, for example,acarine, nematode and mollusc pests. Insects, acarines, nematodes andmolluscs are hereinafter collectively referred to as pests. The pestswhich may be combated and controlled by the use of the inventioncompounds include those pests associated with agriculture (which termincludes the growing of crops for food and fiber products), horticultureand animal husbandry, companion animals, forestry and the storage ofproducts of vegetable origin (such as fruit, grain and timber); thosepests associated with the damage of man-made structures and thetransmission of diseases of man and animals; and also nuisance pests(such as flies).

Examples of the abovementioned animal pests are:

from the order Acarina, for example,

Acalitus spp., Aculus spp., Acaricalus spp., Aceria spp., Acarus siro,Amblyomma spp., Argas spp., Boophilus spp., Brevipalpus spp., Bryobiaspp., Calipitrimerus spp., Chorioptes spp., Dermanyssus gallinae,Dermatophagoides spp., Eotetranychus spp., Eriophyes spp.,Hemitarsonemus spp., Hyalomma spp., Ixodes spp., Olygonychus spp.,Ornithodoros spp., Polyphagotarsone latus, Panonychus spp.,Phyllocoptruta oleivora, Phytonemus spp., Polyphagotarsonemus spp.,Psoroptes spp., Rhipicephalus spp., Rhizoglyphus spp., Sarcoptes spp.,Steneotarsonemus spp., Tarsonemus spp., and Tetranychus spp.;from the order Anoplura, for example,Haematopinus spp., Linognathus spp., Pediculus spp., Pemphigus spp., andPhylloxera spp.;from the order Coleoptera, for example,Agriotes spp., Amphimallon majale, Anomala orientalis, Anthonomus spp.,Aphodius spp., Astylus atromaculatus, Ataenius spp., Atomaria linearis,Chaetocnema tibialis, Cerotoma spp., Conoderus spp., Cosmopolites spp.,Cotinis nitida, Curculio spp., Cyclocephala spp., Dermestes spp.,Diabrotica spp., Diloboderus abderus, Epilachna spp., Eremnus spp.,Heteronychus arator, Hypothenemus hampei, Lagria vilosa, LeptinotarsadecemLineata, Lissorhoptrus spp., Liogenys spp., Maecolaspis spp.,Maladera castanea, Megascelis spp., Melighetes aeneus, Melolontha spp.,Myochrous armatus, Orycaephilus spp., Otiorhynchus spp., Phyllophagaspp., Phlyctinus spp., Popillia spp., Psylliodes spp., Rhyssomatusaubtilis, Rhizopertha spp., Scarabeidae, Sitophilus spp., Sitotrogaspp., Somaticus spp., Sphenophorus spp., Sternechus subsignatus,Tenebrio spp., Tribolium spp., and Trogoderma spp.;from the order Diptera, for example,Aedes spp., Anopheles spp., Antherigona soccata, Bactrocea oleae, Bibiohortulanus, Bradysia spp., Calliphora erythrocephala, Ceratitis spp.,Chrysomyia spp., Culex spp., Cuterebra spp., Dacus spp., Delia spp.,Drosophila melanogaster, Fannia spp., Gastrophilus spp., Geomyzatripunctata, Glossina spp., Hypoderma spp., Hyppobosca spp., Liriomyzaspp., Lucilia spp., Melanagromyza spp., Musca spp., Oestrus spp.,Orseolia spp., Oscinella frit, Pegomyia hyoscyami, Phorbia spp.,Rhagoletis spp., Rivelia quadrifasciata, Scatella spp., Sciara spp.,Stomoxys spp., Tabanus spp., Tannia spp., and Tipula spp.;from the order Hemiptera, for example,Acanthocoris scabrator, Acrosternum spp., Adelphocoris lineolatus,Amblypelta nitida, Bathycoelia thalassina, Blissus spp., Cimex spp.,Clavigralla tomentosicollis, Creontiades spp., Distantiella theobroma,Dichelopsfurcatus, Dysdercus spp., Edessa spp., Euchistus spp., Eurydemapulchrum, Eurygaster spp., Halyomorpha halys, Horcias nobilellus,Leptocorisa spp., Lygus spp., Margarodes spp., Murgantia histrionic,Neomegalotomus spp., Nesidiocoris tenuis, Nezara spp., Nysius simulans,Oebalus insularis, Piesma spp., Piezodorus spp., Rhodnius spp.,Sahlbergella singularis, Scaptocoris castanea, Scotinophara spp.,Thyanta spp., Triatoma spp., Vatiga illudens;Acyrthosium pisum, Adalges spp., Agalliana ensigera, Agonoscenatargionii, Aleurodicus spp., Aleurocanthus spp., Aleurolobus barodensis,Aleurothrixusfloccosus, Aleyrodes brassicae, Amarasca biguttula,Amritodus atkinsoni, Aonidiella spp., Aphididae, Aphis spp., Aspidiotusspp., Aulacorthum solani, Bactericera cockerelli, Bemisia spp.,Brachycaudus spp., Brevicoryne brassicae, Cacopsylla spp., Cavariellaaegopodii Scop., Ceroplaster spp., Chrysomphalus aonidium, Chrysomphalusdictyospermi, Cicadella spp., Cofana spectra, Cryptomyzus spp.,Cicadulina spp., Coccus hesperidum, Dalbulus maidis, Dialeurodes spp.,Diaphorina citri, Diuraphis noxia, Dysaphis spp., Empoasca spp.,Eriosoma larigerum, Erythroneura spp., Gascardia spp., Glycaspisbrimblecombei, Hyadaphis pseudobrassicae, Hyalopterus spp., Hyperomyzuspallidus, Idioscopus clypealis, Jacobiasca lybica, Laodelphax spp.,Lecanium corni, Lepidosaphes spp., Lopaphis erysimi, Lyogenys maidis,Macrosiphum spp., Mahanarva spp., Metcalfa pruinosa, Metopolophiumdirhodum, Myndus crudus, Myzus spp., Neotoxoptera spp., Nephotettixspp., Nilaparvata spp., Nippolachnus piri Mats, Odonaspis ruthae, Oregmalanigera Zehnter, Parabemisia myricae, Paratrioza cockerelli, Parlatoriaspp., Pemphigus spp., Peregrinus maidis, Perkinsiella spp., Phorodonhumuli, Phylloxera spp., Planococcus spp., Pseudaulacaspis spp.,Pseudococcus spp., Pseudatomoscelis seriatus, Psylla spp., Pulvinariaaethiopica, Quadraspidiotus spp., Quesada gigas, Recilia dorsalis,Rhopalosiphum spp., Saissetia spp., Scaphoideus spp., Schizaphis spp.,Sitobion spp., Sogatellafurcifera, Spissistilus festinus, TarophagusProserpina, Toxoptera spp., Trialeurodes spp., Tridiscus sporoboli,Trionymus spp., Trioza erytreae, Unaspis citri, Zyginaflammigera,Zyginidia scutellaris;from the order Hymenoptera, for example,Acromyrmex, Arge spp., Atta spp., Cephus spp., Diprion spp.,Diprionidae, Gilpinia polytoma, Hoplocampa spp., Lasius spp., Monomoriumpharaonis, Neodiprion spp., Pogonomyrmex spp., Slenopsis invicta,Solenopsis spp., and Vespa spp.;from the order Isoptera, for example,Coptotermes spp., Corniternes cumulans, Incisitermes spp., Macrotermesspp., Mastotermes spp., Microtermes spp., Reticulitermes spp.;Solenopsis geminatefrom the order Lepidoptera, for example,Acleris spp., Adoxophyes spp., Aegeria spp., Agrotis spp., Alabamaargillaceae, Amylois spp., Anticarsia gemmatalis, Archips spp.,Argyresthia spp., Argyrotaenia spp., Autographa spp., Bucculatrixthurberiella, Busseola fusca, Cadra cautella, Carposina nipponensis,Chilo spp., Choristoneura spp., Chrysoteuchia topiaria, Clysiaambiguella, Cnaphalocrocis spp., Cnephasia spp., Cochylis spp.,Coleophora spp., Colias lesbia, Cosmophilaflava, Crambus spp.,Crocidolomia binotalis, Cryptophlebia leucotreta, Cydalima perspectalis,Cydia spp., Diaphania perspectalis, Diatraea spp., Diparopsis castanea,Earias spp., Eldana saccharina, Ephestia spp., Epinotia spp., Estigmeneacrea, Etiella zinckinella, Eucosma spp., Eupoecilia ambiguella,Euproctis spp., Euxoa spp., Feltia jaculiferia, Grapholita spp., Hedyanubiferana, Heliothis spp., Hellula undalis, Herpetogramma spp.,Hyphantria cunea, Keiferia lycopersicella, Lasmopalpus lignosellus,Leucoptera scitella, Lithocollethis spp., Lobesia botrana, Loxostegebifidalis, Lymantria spp., Lyonetia spp., Malacosoma spp., Mamestrabrassicae, Manduca sexta, Mythimna spp., Noctua spp., Operophtera spp.,Orniodes indica, Ostrinia nubilalis, Pammene spp., Pandemis spp.,Panolis flammea, Papaipema nebris, Pectinophora gossypiela,Perileucoptera coffeella, Pseudaletia unipuncta, Phthorimaeaoperculella, Pieris rapae, Pieris spp., Plutella xylostella, Prays spp.,Pseudoplusia spp., Rachiplusia nu, Richia albicosta, Scirpophaga spp.,Sesamia spp., Sparganothis spp., Spodoptera spp., Sylepta derogate,Synanthedon spp., Thaumetopoea spp., Tortrix spp., Trichoplusia ni, Tutaabsoluta, and Yponomeuta spp.;from the order Mallophaga, for example,Damalinea spp., and Trichodectes spp.;from the order Orthoptera, for example,Blatta spp., Blattella spp., Gryllotalpa spp., Leucophaea maderae,Locusta spp., Neocurtilla hexadactyla, Periplaneta spp., Scapteriscusspp., and Schistocerca spp.;from the order Psocoptera, for example,Liposcelis spp.;from the order Siphonaptera, for example,Ceratophyllus spp., Ctenocephalides spp., and Xenopsylla cheopis;from the order Thysanoptera, for example,Calliothrips phaseoli, Frankliniella spp., Heliothrips spp.,Hercinothrips spp., Parthenothrips spp., Scirtothrips aurantii,Sericothrips variabilis, Taeniothrips spp., Thrips spp.;from the order Thysanura, for example,Lepisma saccharina.

The active ingredients according to the invention can be used forcontrolling, i.e. containing or destroying, pests of the abovementionedtype which occur in particular on plants, especially on useful plantsand ornamentals in agriculture, in horticulture and in forests, or onorgans, such as fruits, flowers, foliage, stalks, tubers or roots, ofsuch plants, and in some cases even plant organs which are formed at alater point in time remain protected against these pests.

Suitable target crops are, in particular, cereals, such as wheat,barley, rye, oats, rice, maize or sorghum; beet, such as sugar or fodderbeet; fruit, for example pomaceous fruit, stone fruit or soft fruit,such as apples, pears, plums, peaches, almonds, cherries or berries, forexample strawberries, raspberries or blackberries; leguminous crops,such as beans, lentils, peas or soya; oil crops, such as oilseed rape,mustard, poppies, olives, sunflowers, coconut, castor, cocoa or groundnuts; cucurbits, such as pumpkins, cucumbers or melons; fibre plants,such as cotton, flax, hemp or jute; citrus fruit, such as oranges,lemons, grapefruit or tangerines; vegetables, such as spinach, lettuce,asparagus, cabbages, carrots, onions, tomatoes, potatoes or bellpeppers; Lauraceae, such as avocado, Cinnamonium or camphor; and alsotobacco, nuts, coffee, eggplants, sugarcane, tea, pepper, grapevines,hops, the plantain family, latex plants and ornamentals.

The invention therefore provides a method of combating and controllinginsects, acarines, nematodes or molluscs which comprises applying aninsecticidally, acaricidally, nematicidally or molluscicidally effectiveamount of a compound of formula (I), or a composition containing acompound of formula (I), to a pest, a locus of pest, preferably a plant,or to a plant susceptible to attack by a pest, The compounds of formula(I) are preferably used against insects, acarines or nematodes.

As for acari, for example, Tetranychus cinnabarinus, Tetranychusurticae, Panonychus citri, Aculops pelekassi, Tarsonemus spp.

As for nematodes, for example, Meloidogyne incognita, Bursaphelenchuslignicolus Mamiya et Kiyohara, Aphelenchoides besseyi, Heteroderaglycines, Pratylenchus spp.

Additionally, the compounds can be used for controlling animal pests, inparticular insects, arachnids, helminths, nematodes and molluscs, whichare encountered in agriculture, in horticulture, the field of veterinarymedicine, in forests, in gardens and leisure facilities, in theprotection of stored products and of materials, and in the hygienesector. They may preferably be employed as plant protection agents. Theymay be active against normally sensitive and resistant species andagainst all or some stages of development.

These pests include inter alia:

From the order of the Anoplura (Phthiraptera), for example, Damaliniaspp., Haematopinus spp., Linognathus spp., Pediculus spp., Trichodectesspp.

From the class of the Arachnida, for example, Acarus siro, Aceriasheldoni, Aculops spp., Aculus spp., Amblyomma spp., Argas spp.,Boophilus spp., Brevipalpus spp., Bryobia praetiosa, Chorioptes spp.,Dermanyssus gallinae, Eotetranychus spp., Epitrimerus pyri,Eutetranychus spp., Eriophyes spp., Hemitarsonemus spp., Hyalomma spp.,Ixodes spp., Latrodectus mactans, Metatetranychus spp., Oligonychusspp., Ornithodoros spp., Panonychus spp., Phyllocoptruta oleivora,Polyphagotarsonemus latus, Psoroptes spp., Rhipicephalus spp.,Rhizoglyphus spp., Sarcoptes spp., Scorpio maurus, Stenotarsonemus spp.,Tarsonemus spp., Tetranychus spp., Vasates lycopersici.

From the class of the Bivalva, for example, Dreissena spp.

From the order of the Chilopoda, for example, Geophilus spp., Scutigeraspp.

From the order of the Coleoptera, for example, Acanthoscehdes obtectus,Adoretus spp., Agelastica alni, Agriotes spp., Amphimallon solstitialis,Anobium punctatum, Anoplophora spp., Anthonomus spp., Anthrenus spp.,Apogonia spp., Atomaria spp., Attagenus spp., Bruchidius obtectus,Bruchus spp., Ceuthorhynchus spp., Cleonus mendicus, Conoderus spp.,Cosmopolites spp., Costelytra zealandica, Curculio spp., Cryptorhynchuslapathi, Dermestes spp., Diabrotica spp., Epilachna spp., Faustinuscubae, Gibbium psylloides, Heteronychus arator, Hylamorpha elegans,Hylotrupes bajulus, Hypera postica, Hypothenemus spp., Lachnosternaconsanguinea, Leptinotarsa decemlineata, Lissorhoptrus oryzophilus,Lixus spp., Lyctus spp., Meligethes aeneus, Melolontha melolontha,Migdolus spp., Monochamus spp., Naupactus xanthographus, Niptushololeucus, Oryctes rhinoceros, Oryzaephilus surinamensis, Otiorrhynchussulcatus, Oxycetonia jucunda, Phaedon cochleariae, Phyllophaga spp.,Popillia japonica, Premnotrypes spp., Psylliodes chrysocephala, Ptinusspp., Rhizobius ventralis, Rhizopertha dominica, Sitophilus spp.,Sphenophorus spp., Sternechus spp., Symphyletes spp., Tenebrio molitor,Tribolium spp., Trogoderma spp., Tychius spp., Xylotrechus spp., Zabrusspp.

From the order of the Collembola, for example, Onychiurus armatus.

From the order of the Dermaptera, for example, Forficula auricularia.

From the order of the Diplopoda, for example, Blaniulus guttulatus.

From the order of the Diptera, for example, Aedes spp., Anopheles spp.,Bibio hortulanus, Calliphora erythrocephala, Ceratitis capitata,Chrysomyia spp., Cochliomyia spp., Cordylobia anthropophaga, Culex spp.,Cuterebra spp., Dacus oleae, Dermatobia hominis, Drosophila spp., Fanniaspp., Gastrophilus spp., Hylemyia spp., Hyppobosca spp., Hypoderma spp.,Liriomyza spp., Lucilia spp., Musca spp., Nezara spp., Oestrus spp.,Oscinella frit, Pegomyia hyoscyami, Phorbia spp., Stomoxys spp., Tabanusspp., Tannia spp., Tipula paludosa, Wohlfahrtia spp.

From the class of the Gastropoda, for example, Arion spp., Biomphalariaspp., Bulinus spp., Deroceras spp., Galba spp., Lymnaea spp.,Oncomelania spp., Succinea spp.

From the class of the helminths, for example, Ancylostoma duodenale,Ancylostoma ceylanicum, Acylostoma braziliensis, Ancylostoma spp.,Ascaris lumbricoides, Ascaris spp., Brugia malayi, Brugia timori,Bunostomum spp., Chabertia spp., Clonorchis spp., Cooperia spp.,Dicrocoelium spp., Dictyocaulusfilaria, Diphyllobothrium latum,Dracunculus medinensis, Echinococcus granulosus, Echinococcusmultilocularis, Enterobius vermicularis, Faciola spp., Haemonchus spp.,Heterakis spp., Hymenolepis nana, Hyostrongulus spp., Loa Loa,Nematodirus spp., Oesophagostomum spp., Opisthorchis spp., Onchocercavolvulus, Ostertagia spp., Paragonimus spp., Schistosomen spp.,Strongyloides fuelleborni, Strongyloides stercoralis, Stronyloides spp.,Taenia saginata, Taenia solium, Trichinella spiralis, Trichinellanativa, Trichinella britovi, Trichinella nelsoni, Trichinellapseudopsiralis, Trichostrongulus spp., Trichuris trichiura, Wuchereriabancrofti.

It may be furthermore possible to control protozoa, such as Eimeria.

From the order of the Heteroptera, for example, Anasa tristis,Antestiopsis spp., Blissus spp., Calocoris spp., Campylomma livida,Cavelerius spp., Cimex spp., Creontiades dilutus, Dasynus piperis,Dichelopsfurcatus, Diconocoris hewetti, Dysdercus spp., Euschistus spp.,Eurygaster spp., Heliopeltis spp., Horcias nobilellus, Leptocorisa spp.,Leptoglossus phyllopus, Lygus spp., Macropes excavatus, Miridae, Nezaraspp., Oebalus spp., Pentomidae, Piesma quadrata, Piezodorus spp.,Psallus seriatus, Pseudacysta persea, Rhodnius spp., Sahlbergellasingularis, Scotinophora spp., Stephanitis nashi, Tibraca spp., Triatomaspp.

From the order of the Homoptera, for example, Acyrthosipon spp.,Aeneolamia spp., Agonoscena spp., Aleurodes spp., Aleurolobusbarodensis, Aleurothrixus spp., Amrasca spp., Anuraphis cardui,Aonidiella spp., Aphanostigma piri, Aphis spp., Arboridia apicalis,Aspidiella spp., Aspidiotus spp., Atanus spp., Aulacorthum solani,Bemisia spp., Brachycaudus helichrysii, Brachycolus spp., Brevicorynebrassicae, Calligypona marginata, Carneocephala fulgida, Ceratovacunalanigera, Cercopidae, Ceroplastes spp., Chaetosiphon fragaefolii,Chionaspis tegalensis, Chlorita onukii, Chromaphis juglandicola,Chrysomphalusficus, Cicadulina mbila, Coccomytilus halli, Coccus spp.,Cryptomyzus ribis, Dalbulus spp., Dialeurodes spp., Diaphorina spp.,Diaspis spp., Doralis spp., Drosicha spp., Dysaphis spp., Dysmicoccusspp., Empoasca spp., Eriosoma spp., Erythroneura spp., Euscelisbilobatus, Geococcus coffeae, Homalodisca coagulata, Hyalopterusarundinis, Icerya spp., Idiocerus spp., Idioscopus spp., Laodelphaxstriatellus, Lecanium spp., Lepidosaphes spp., Lipaphis erysimi,Macrosiphum spp., Mahanarva fimbriolata, Melanaphis sacchari,Metcalfiella spp., Metopolophium dirhodum, Monellia costalis,Monelliopsis pecanis, Myzus spp., Nasonovia ribisnigri, Nephotettixspp., Nilaparvata lugens, Oncometopia spp., Orthezia praelonga,Parabemisia myricae, Paratrioza spp., Parlatoria spp., Pemphigus spp.,Peregrinus maidis, Phenacoccus spp., Phloeomyzus passerinii, Phorodonhumuli, Phylloxera spp., Pinnaspis aspidistrae, Planococcus spp.,Protopulvinaria pyriformis, Pseudaulacaspis pentagona, Pseudococcusspp., Psylla spp., Pteromalus spp., Pyrilla spp., Quadraspidiotus spp.,Quesada gigas, Rastrococcus spp., Rhopalosiphum spp., Saissetia spp.,Scaphoides titanus, Schizaphis graminum, Selenaspidus articulatus,Sogata spp., Sogatella furcifera, Sogatodes spp., Stictocephala festina,Tenalaphara malayensis, Tinocallis caryaefoliae, Tomaspis spp.,Toxoptera spp., Trialeurodes vaporariorum, Trioza spp., Typhlocyba spp.,Unaspis spp., Viteus vitifolii.

From the order of the Hymenoptera, for example, Diprion spp., Hoplocampaspp., Lasius spp., Mono-morium pharaonis, Vespa spp.

From the order of the Isopoda, for example, Armadillidium vulgare,Oniscus asellus, Porcellio scaber.

From the order of the Isoptera, for example, Reticulitermes spp.,Odontotermes spp.

From the order of the Lepidoptera, for example, Acronicta major, Aedialeucomelas, Agrotis spp., Alabama argillacea, Anticarsia spp., Barathrabrassicae, Bucculatrix thurberiella, Bupalus piniarius, Cacoecia podana,Capua reticulana, Carpocapsa pomonella, Cheimatobia brumata, Chilo spp.,Choristoneurafumiferana, Clysia ambiguella, Cnaphalocerus spp., Eariasinsulana, Ephestia kuehniella, Euproctis chrysorrhoea, Euxoa spp.,Feltia spp., Galleria mellonella, Helicoverpa spp., Heliothis spp.,Hofinannophila pseudospretella, Homona magnanima, Hyponomeuta padella,Laphygma spp., Lithocolletis blancardella, Lithophane antennata,Loxagrotis albicosta, Lymantria spp., Malacosoma neustria, Mamestrabrassicae, Mocis repanda, Mythimna separata, Oria spp., Oulema oryzae,Panolisflammea, Pectinophora gossypiella, Phyllocnistis citrella, Pierisspp., Plutella xylostella, Prodenia spp., Pseudaletia spp., Pseudoplusiaincludens, Pyrausta nubilalis, Spodoptera spp., Thermesia gemmatalis,Tinea pellionella, Tineola bisselliella, Tortrix viridana, Trichoplusiaspp.

From the order of the Orthoptera, for example, Acheta domesticus, Blattaorientalis, Blattella germanica, Gryllotalpa spp., Leucophaea maderae,Locusta spp., Melanoplus spp., Periplaneta americana, Schistocercagregaria.

From the order of the Siphonaptera, for example, Ceratophyllus spp.,Xenopsylla cheopis.

From the order of the Symphyla, for example, Scutigerella immaculata.

From the order of the Thysanoptera, for example, Baliothrips biformis,Enneothripsflavens, Frankliniella spp., Heliothrips spp., Hercinothripsfemoralis, Kakothrips spp., Rhipiphorothrips cruentatus, Scirtothripsspp., Taeniothrips cardamoni, Thrips spp.

From the order of the Thysanura, for example, Lepisma saccharina.

The phytoparasitic nematodes include, for example, Anguina spp.,Aphelenchoides spp., Belonoaimus spp., Bursaphelenchus spp., Ditylenchusdipsaci, Globodera spp., Heliocotylenchus spp., Heterodera spp.,Longidorus spp., Meloidogyne spp., Pratylenchus spp., Radopholussimilis, Rotylenchus spp., Trichodorus spp., Tylenchorhynchus spp.,Tylenchulus spp., Tylenchulus semipenetrans, Xiphinema spp.

Furthermore, in the field of veterinary medicine, the novel compounds ofthe present invention can be effectively used against various harmfulanimal parasitic pests (endoparasites and ectoparasites), for example,insects and helminthes.

Examples of such animal parasitic pests include the pests as describedbelow.

Examples of the insects include Gasterophilus spp., Stomoxys spp.,Trichodectes spp., Rhodnius spp., Ctenocephalides canis, Cimx lecturius,Ctenocephalides felis, Lucilia cuprina, and the like.

Examples of acari include Ornithodoros spp., Ixodes spp., Boophilusspp., and the like.

In the veterinary fields, e.g. in the field of veterinary medicine, theactive compounds according to the present invention are active againstanimal parasites, in particular ectoparasites or endoparasites.

The term endoparasites includes in particular helminths, such ascestodes, nematodes or trematodes, and protozoae, such as coccidia.

Ectoparasites are typically and preferably arthropods, in particularinsects such as flies (stinging and licking), parasitic fly larvae,lice, hair lice, bird lice, fleas and the like; or acarids, such asticks, for examples hard ticks or soft ticks, or mites, such as scabmites, harvest mites, bird mites and the like.

These parasites include:

From the order of the Anoplurida, for example Haematopinus spp.,Linognathus spp., Pediculus spp., Phtirus spp., Solenopotes spp.;particular examples are: Linognathus setosus, Linognathus vituli,Linognathus ovillus, Linognathus oviformis, Linognathus pedalis,Linognathus stenopsis, Haematopinus asini macrocephalus, Haematopinuseurysternus, Haematopinus suis, Pediculus humanus capitis, Pediculushumanus corporis, Phylloera vastatrix, Phthirus pubis, Solenopotescapillatus; from the order of the Mallophagida and the subordersAmblycerina and Ischnocerina, for example Trimenopon spp., Menopon spp.,Trinoton spp., Bovicola spp., Werneckiella spp., Lepikentron spp.,Damalina spp., Trichodectes spp., Felicola spp.; particular examplesare: Bovicola bovis, Bovicola ovis, Bovicola limbata, Damalina bovis,Trichodectes canis, Felicola subrostratus, Bovicola caprae, Lepikentronovis, Werneckiella equi; from the order of the Diptera and the subordersNematocerina and Brachycerina, for example Aedes spp., Anopheles spp.,Culex spp., Simulium spp., Eusimulium spp., Phlebotomus spp., Lutzomyiaspp., Culicoides spp., Chrysops spp., Odagmia spp., Wilhelmia spp.,Hybomitra spp., Atylotus spp., Tabanus spp., Haematopota spp.,Philipomyia spp., Braula spp., Musca spp., Hydrotaea spp., Stomoxysspp., Haematobia spp., Morellia spp., Fannia spp., Glossina spp.,Calliphora spp., Lucilia spp., Chrysomyia spp., Wohlfahrtia spp.,Sarcophaga spp., Oestrus spp., Hypoderma spp., Gasterophilus spp.,Hippobosca spp., Lipoptena spp., Melophagus spp., Rhinoestrus spp.,Tipula spp.; particular examples are: Aedes aegypti, Aedes albopictus,Aedes taeniorhynchus, Anopheles gambiae, Anopheles maculipennis,Calliphora erythrocephala, Chrysozona pluvialis, Culex quinquefasciatus,Culex pipiens, Culex tarsalis, Fannia canicularis, Sarcophaga carnaria,Stomoxys calcitrans, Tipula paludosa, Lucilia cuprina, Lucilia sericata,Simulium reptans, Phlebotomus papatasi, Phlebotomus longipalpis, Odagmiaornata, Wilhelmia equina, Boophthora erythrocephala, Tabanus bromius,Tabanus spodopterus, Tabanus atratus, Tabanus sudeticus, Hybomitraciurea, Chrysops caecutiens, Chrysops relictus, Haematopota pluvialis,Haematopota italica, Musca autumnalis, Musca domestica, Haematobiairritans irritans, Haematobia irritans exigua, Haematobia stimulans,Hydrotaea irritans, Hydrotaea albipuncta, Chrysomya chloropyga,Chrysomya bezziana, Oestrus ovis, Hypoderma bovis, Hypoderma lineatum,Przhevalskiana silenus, Dermatobia hominis, Melophagus ovinus, Lipoptenacapreoli, Lipoptena cervi, Hippobosca variegata, Hippobosca equina,Gasterophilus intestinalis, Gasterophilus haemorroidalis, Gasterophilusinermis, Gasterophilus nasalis, Gasterophilus nigricornis, Gasterophiluspecorum, Braula coeca; from the order of the Siphonapterida, for examplePulex spp., Ctenocephalides spp., Tunga spp., Xenopsylla spp.,Ceratophyllus spp.; particular examples are: Ctenocephalides canis,Ctenocephalides felis, Pulex irritans, Tunga penetrans, Xenopsyllacheopis; from the order of the Heteropterida, for example Cimex spp.,Triatoma spp., Rhodnius spp., Panstrongylus spp.

From the order of the Blattarida, for example Blatta orientalis,Periplaneta americana, Blattela germanica, Supella spp., (e.g. Suppellalongipalpa);

From the subclass of the Acari (Acarina) and the orders of the Meta- andMesostigmata, for example Argas spp., Ornithodorus spp., Otobius spp.,Ixodes spp., Amblyomma spp., Rhipicephalus (Boophilus) spp., Dermacentorspp., Haemophysalis spp., Hyalomma spp., Dermanyssus spp., Rhipicephalusspp., (the original genus of multi host ticks) Ornithonyssus spp.,Pneumonyssus spp., Raillietia spp., Pneumonyssus spp., Sternostoma spp.,Varroa spp., Acarapis spp.; particular examples are: Argas persicus,Argas reflexus, Ornithodorus moubata, Otobius megnini, Rhipicephalus(Boophilus) microplus, Rhipicephalus (Boophilus) decoloratus,Rhipicephalus (Boophilus) annulatus, Rhipicephalus (Boophilus)calceratus, Hyalomma anatolicum, Hyalomma aegypticum, Hyalommamarginatum, Hyalomma transiens, Rhipicephalus evertsi, Ixodes ricinus,Ixodes hexagonus, Ixodes canisuga, Ixodes pilosus, Ixodes rubicundus,Ixodes scapularis, Ixodes holocyclus, Haemaphysalis concinna,Haemaphysalis punctata, Haemaphysalis cinnabarina, Haemaphysalisotophila, Haemaphysalis leachi, Haemaphysalis longicorni, Dermacentormarginatus, Dermacentor reticulatus, Dermacentor pictus, Dermacentoralbipictus, Dermacentor andersoni, Dermacentor variabilis, Hyalommamauritanicum, Rhipicephalus sanguineus, Rhipicephalus bursa,Rhipicephalus appendiculatus, Rhipicephalus capensis, Rhipicephalusturanicus, Rhipicephalus zambeziensis, Amblyomma americanum, Amblyommavariegatum, Amblyomma maculatum, Amblyomma hebraeum, Amblyommacajennense, Dermanyssus gallinae, Ornithonyssus bursa, Ornithonyssussylviarum, Varroa jacobsoni; from the order of the Actinedida(Prostigmata) and Acaridida (Astigmata), for example Acarapis spp.,Cheyletiella spp., Ornithocheyletia spp., Myobia spp., Psorergates spp.,Demodex spp., Trombicula spp., Listrophorus spp., Acarus spp.,Tyrophagus spp., Caloglyphus spp., Hypodectes spp., Pterolichus spp.,Psoroptes spp., Chorioptes spp., Otodectes spp., Sarcoptes spp.,Notoedres spp., Knemidocoptes spp., Cytodites spp., Laminosioptes spp.;particular examples are: Cheyletiella yasguri, Cheyletiella blakei,Demodex canis, Demodex bovis, Demodex ovis, Demodex caprae, Demodexequi, Demodex caballi, Demodex suis, Neotrombicula autumnalis,Neotrombicula desaleri, Neoschongastia xerothermobia, Trombiculaakamushi, Otodectes cynotis, Notoedres cati, Sarcoptis canis, Sarcoptesbovis, Sarcoptes ovis, Sarcoptes rupicaprae (S. caprae), Sarcoptes equi,Sarcoptes suis, Psoroptes ovis, Psoroptes cuniculi, Psoroptes equi,Chorioptes bovis, Psoergates ovis, Pneumonyssoidic mange,Pneumonyssoides caninum, Acarapis woodi.

The active compounds according to the invention are also suitable forcontrolling arthropods, helminths and protozoae, which attack animals.

Animals include agricultural livestock such as, for example, cattle,sheep, goats, horses, pigs, donkeys, camels, buffaloes, rabbits,chickens, turkeys, ducks, geese, cultured fish, honeybees.

Moreover, animals include domestic animals—also referred to as companionanimals—such as, for example, dogs, cats, cage birds, aquarium fish andwhat are known as experimental animals such as, for example, hamsters,guinea pigs, rats and mice.

By controlling these arthropods, helminths and/or protozoae, it isintended to reduce deaths and improve performance (in the case of meat,milk, wool, hides, eggs, honey and the like) and health of the hostanimal, so that more economical and simpler animal keeping is madepossible by the use of the active compounds according to the invention.

For example, it may be desirable to prevent or interrupt the uptake ofblood by the parasites from the hosts.

Also, controlling the parasites may help to prevent the transmittance ofinfectious agents.

The term “controlling” as used herein with regard to the veterinaryfield, means that the active compounds are effective in reducing theincidence of the respective parasite in an animal infected with suchparasites to innocuous levels.

More specifically, “controlling”, as used herein, means that the activecompound is effective in killing the respective parasite, inhibiting itsgrowth, or inhibiting its proliferation. Generally, when used for thetreatment of animals the active compounds according to the invention canbe applied directly.

Preferably they are applied as pharmaceutical compositions which maycontain pharmaceutically acceptable excipients and/or auxiliaries whichare known in the art.

In the veterinary field and in animal keeping, the active compounds areapplied (e.g. administered) in the known manner by enteraladministration in the form of, for example, tablets, capsules, drinks,drenches, granules, pastes, boluses, the feed-through method,suppositories; by parenteral administration, such as, for example, byinjections (intramuscular, subcutaneous, intravenous, intraperitonealand the like), implants, by nasal application, by dermal application inthe form of, for example, bathing or dipping, spraying, pouring-on andspotting-on, washing, dusting, and with the aid ofactive-compound-comprising shaped articles such as collars, ear tags,tail tags, limb bands, halters, marking devices and the like.

The active compounds may be formulated as shampoo or as suitableformulations usable in aerosols, unpressurized sprays, for example pumpsprays and atomizer sprays.

When used for livestock, poultry, domestic animals and the like, theactive compounds according to the invention can be applied asformulations (for example powders, wettable powders [“WP”], emulsions,emulsifiable concentrates [“EC”], flowables, homogeneous solutions, andsuspension concentrates [“SC”]) which comprise the active compounds inan amount of from 1 to 80 percent by weight, either directly or afterdilution (e.g. 100- to 10 000-fold dilution), or else as a chemicalbath.

When used in the veterinary field the active compounds according to theinvention may be used in combination with suitable synergists or otheractive compounds, such as for example, acaricides, insecticides,anthelmintics, anti-protozoal drugs.

In the present invention, a substance having an insecticidal actionagainst pests including all of these is referred to as an insecticide.

An active compound of the present invention can be prepared inconventional formulation forms, when used as an insecticide.

Examples of the formulation forms include solutions, emulsions, wettablepowders, water dispersible granules, suspensions, powders, foams,pastes, tablets, granules, aerosols, active compound-infiltrated naturaland synthetic materials, microcapsules, seed coating agents,formulations used with a combustion apparatus (for example, fumigationand smoking cartridges, cans, coils or the like as the combustionapparatus), ULV (cold mist, warm mist), and the like.

These formulations can be produced by methods that are known per se.

For example, a formulation can be produced by mixing the active compoundwith a developer, that is, a liquid diluent or carrier; a liquefied gasdiluent or carrier; a solid diluent or carrier, and optionally with asurfactant, that is, an emulsifier and/or dispersant and/or foamingagent.

In the case where water is used as the developer, for example, anorganic solvent can also be used as an auxiliary solvent.

Examples of the liquid diluent or carrier include aromatic hydrocarbons(for example, xylene, toluene, alkylnaphthalene and the like),chlorinated aromatic or chlorinated aliphatic hydrocarbons (for example,chlorobenzenes, ethylene chlorides, methylene chlorides), aliphatichydrocarbons (for example, cyclohexanes), paraffins (for example,mineral oil fractions), alcohols (for example, butanol, glycols andtheir ethers, esters and the like), ketones (for example, acetone,methyl ethyl ketone, methyl isobutyl ketone, cyclohexanone and thelike), strongly polar solvents (for example, dimethylformamide,dimethylsulfoxide and the like), water and the like. The liquefied gasdiluent or carrier may be those which are gaseous at normal temperatureand normal pressure, for example, aerosol propellants such as butane,propane, nitrogen gas, carbon dioxide and halogenated hydrocarbons.Examples of the solid diluent include pulverized natural minerals (forexample, kaolin, clay, talc, chalk, quartz, attapulgite,montmorillonite, diatomaceous earth, and the like), pulverized syntheticminerals (for example, highly dispersed silicic acid, alumina, silicatesand the like), and the like. Examples of the solid carrier for granulesinclude pulverized and screened rocks (for example, calcite, marble,pumice, sepiolite, dolomite and the like), synthetic granules ofinorganic and organic powder, fine particles of organic materials (forexample, sawdust, coconut shells, maize cobs, tobacco stalk and thelike), and the like. Examples of the emulsifier and/or foaming agentinclude nonionic and anionic emulsifiers [for example, polyoxyethylenefatty acid esters, polyoxyethylene fatty acid alcohol ethers (forexample, alkylaryl polyglycol ether), alkylsulfonates, alkylsulfates,arylsulfonates and the like], albumin hydro lyzate, and the like.Examples of the dispersant include lignin sulfite waste liquor andmethylcellulose.

Fixing agents can also be used in the formulations (powders, granules,emulsions), and examples of the fixing agent includecarboxymethylcellulose, natural and synthetic polymers (for example, gumarabic, polyvinyl alcohol, polyvinyl acetate, and the like) and thelike. Colorants can also be used, and examples of the colorants includeinorganic pigments (for example, iron oxide, titanium oxide, PrussianBlue and the like), organic dyes such as alizarin dyes, azo dyes ormetal phthalocyanine dyes, and in addition, trace elements such as thesalts of iron, manganese, boron, copper, cobalt, molybdenum and zinc.The formulations in general can contain the active ingredient in anamount ranging from 0.1 to 95 percent by weight, and preferably 0.5 to90 percent> by weight. The compound according to the present inventioncan also exist as an admixture with other active compounds, for example,insecticides, poisonous baits, bactericides, miticides, nematicides,fungicides, growth regulators, herbicides and the like, in the form oftheir commercially useful formulation forms and in the application formsprepared from those formulations.

The content of the compound according to the present invention in acommercially useful application form can be varied within a wide range.

The concentration of the active compound according to the presentinvention in actual usage can be, for example, in the range of 0.0000001to 100 percent by weight, and preferably 0.00001 to 1 percent by weight.

The compounds according to the present invention can be used throughconventional methods that are appropriate for the usage form.

The active compound of the present invention have, when used againsthygiene pests and pests associated with stored products, stabilityeffective against alkali on lime materials, and also shows excellentresidual effectiveness on wood and soil. The compounds of the inventionmay have favourable properties with respect to amount applied, residueformulation, selectivity, toxicity, production methodology, highactivity, wide spectrum of control, safety, control of resistantorganisms, e.g. pests that are resistant to organic phosphorus agentsand/or carbamate agents.

Further embodiments of the invention are described below.

The compounds of formula (I) can be used to combat and controlinfestations of insect pests such as Lepidoptera, Diptera, Hemiptera,Thysanoptera, Orthoptera, Dictyoptera, Coleoptera, Siphonaptera,Hymenoptera and Isoptera and also other invertebrate pests, for example,acarine, nematode and mollusc pests. Insects, acarines, nematodes andmolluscs are hereinafter collectively referred to as pests. The pestswhich may be combated and controlled by the use of the inventioncompounds include those pests associated with agriculture (which termincludes the growing of crops for food and fiber products), horticultureand animal husbandry, companion animals, forestry and the storage ofproducts of vegetable origin (such as fruit, grain and timber); thosepests associated with the damage of man-made structures and thetransmission of diseases of man and animals; and also nuisance pests(such as flies).

The compounds of the invention may be used for example on turf,ornamentals, such as flowers, shrubs, broad-leaved trees or evergreens,for example conifers, as well as for tree injection, pest management andthe like.

The compounds of the invention may be used to control animal housingpests including: Ants, Bedbugs (adult), Bees, Beetles, Boxelder Bugs,Carpenter Bees, Carpet Beetles, Centipedes, Cigarette, Beetles, CloverMites, Cockroaches, Confused Flour Beetle, Crickets, Earwigs, Firebrats,Fleas, Flies, Lesser Grain Borers, Millipedes, Mosquitoes, Red FlourBeetles, Rice Weevils, Saw-toothed Grain Beetles, Silverfish, Sowbugs,Spiders, Termites, Ticks, Wasps, Cockroaches, Crickets, Flies, LitterBeetles (such as Darkling, Hide, and Carrion), Mosquitoes, Pillbugs,Scorpions, Spiders, Spider Mites (Twospotted, Spruce), Ticks.

The compounds of the invention may be used to control ornamental pestsincluding: Ants (Including Imported fire ants), Armyworms, Azaleacaterpillars, Aphids, Bagworms, Black vine weevils (adult), Boxelderbugs, Budworms, California oakworms, Cankerworms, Cockroaches, Crickets,Cutworms, Eastern tent caterpillars, Elm leaf beetles, Europeansawflies, Fall webworms, Flea beetles, Forest tent caterpillars, Gypsymoth larvae, Japanese beetles (adults), June beetles (adults), Lacebugs, Leaf-feeding caterpillars, Leafhoppers, Leafminers (adults), Leafrollers, Leaf skeletonizers, Midges, Mosquitoes, Oleander moth larvae,Pillbugs, Pine sawflies, Pine shoot beetles, Pinetip moths, Plant bugs,Root weevils, Sawflies, Scale insects (crawlers), Spiders, Spittlebugs,Striped beetles, Striped oakworms, Thrips, Tip moths, Tussock mothlarvae, Wasps, Broadmites, Brown softscales, California redscales(crawlers), Clover mites, Mealybugs, Pineneedlescales (crawlers), Spidermites, Whiteflies

The compounds of the invention may be used to control turf pestsincluding: Ants (Including Imported fire ants, Armyworms, Centipedes,Crickets, Cutworms, Earwigs, Fleas (adult), Grasshoppers, Japanesebeetles (adult), Millipedes, Mites, Mosquitoes (adult), Pillbugs, Sodwebworms, Sow bugs, Ticks (including species which transmit Lymedisease), Bluegrass billbugs (adult), Black turfgrass ataenius (adult),Chiggers, Fleas (adult), Grubs (suppression), Hyperodes weevils (adult),Mole crickets (nymphs and young adults), Mole Crickets (mature adults),Chinch Bugs

Examples of pest species which may be controlled by the compounds offormula (I) include: Myzus persicae (aphid), Aphis gossypii (aphid),Aphisfabae (aphid), Lygus spp., (capsids), Dysdercus spp., (capsids),Nilaparvata lugens (planthopper), Nephotettixc incticeps (leafhopper),Nezara spp., (stinkbugs), Euschistus spp., (stinkbugs), Leptocorisaspp., (stinkbugs), Frankliniella occidentalis (thrip), Thrips spp.,(thrips), Leptinotarsa decemlineata (Colorado potato beetle), Anthonomusgrandis (boll weevil), Aonidiella spp., (scale insects), Trialeurodesspp., (white flies), Bemisia tabaci (white fly), Ostrinia nubilalis(European corn borer), Spodoptera littoralis (cotton leafworm),Heliothis virescens (tobacco budworm), Helicoverpa armigera (cottonbollworm), Helicoverpa zea (cotton bollworm), Sylepta derogata (cottonleaf roller), Pieris brassicae (white butterfly), Plutella xylostella(diamond back moth), Agrotis spp., (cutworms), Chilo suppressalis (ricestem borer), Locusta_migratoria (locust), Chortiocetes terminifera(locust), Diabrotica spp., (rootworms), Panonychus ulmi (European redmite), Panonychus citri (citrus red mite), Tetranychus urticae(two-spotted spider mite), Tetranychus cinnabarinus (carmine spidermite), Phyllocoptruta oleivora (citrus rust mite), Polyphagotarsonemuslatus (broad mite), Brevipalpus spp., (flat mites), Boophilus microplus(cattle tick), Dermacentor variabilis (American dog tick),Ctenocephalides felis (cat flea), Liriomyza spp., (leafminer), Muscadomestica (housefly), Aedes aegypti (mosquito), Anopheles spp.,(mosquitoes), Culex spp., (mosquitoes), Lucillia spp., (blowflies),Blattella germanica (cockroach), Periplaneta americana (cockroach),Blatta orientalis (cockroach), termites of the Mastotermitidae (forexample Mastotermes spp.), the Kalotermitidae (for example Neotermesspp.), the Rhinotermitidae (for example Coptotermes formosanus,Reticulitermes flavipes, R. speratu, R. virginicus, R. hesperus, and R.santonensis) and the Termitidae (for example Globitermes sulfureus),Solenopsis geminata (fire ant), Monomorium pharaonis (pharaoh's ant),Damalinia spp., and Linognathus spp., (biting and sucking lice),Meloidogyne spp., (root knot nematodes), Globodera spp., and Heteroderaspp., (cyst nematodes), Pratylenchus spp., (lesion nematodes),Rhodopholus spp., (banana burrowing nematodes), Tylenchulus spp. (citrusnematodes), Haemonchus contortus (barber pole worm), Caenorhabditiselegans_(vinegar eelworm), Trichostrongylus spp., (gastro intestinalnematodes) and Deroceras reticulatum (slug).

The compounds of the invention may be used for pest control on variousplants, including soybean (e.g. in some cases 10-70 g/ha), corn (e.g. insome cases 10-70 g/ha), sugarcane (e.g. in some cases 20-200 g/ha),alfalfa (e.g. in some cases 10-70 g/ha), brassicas (e.g. in some cases10-50 g/ha), oilseed rape (e.g. canola) (e.g. in some cases 20-70 g/ha),potatoes (including sweet potatoes) (e.g. in some cases 10-70 g/ha),cotton (e.g. in some cases 10-70 g/ha), rice (e.g. in some cases 10-70g/ha), coffee (e.g. in some cases 30-150 g/ha), citrus (e.g. in somecases 60-200 g/ha), almonds (e.g. in some cases 40-180 g/ha), fruitingvegetables (e.g. tomatoes, pepper, chili, eggplant, cucumber, squashetc.) (e.g. in some cases 10-80 g/ha), tea (e.g. in some cases 20-150g/ha), bulb vegetables (e.g. onion, leek etc.) (e.g. in some cases 30-90g/ha), grapes (e.g. in some cases 30-180 g/ha), pome fruit (e.g. apples,pears etc.) (e.g. in some cases 30-180 g/ha), and stone fruit (e.g.pears, plums etc.) (e.g. in some cases 30-180 g/ha).

The compounds of the invention may be used on soybean to control, forexample, Elasmopalpus lignosellus, Diloboderus abderus, Diabroticaspeciosa, Sternechus subsignatus, Formicidae, Agrotis ipsilon, Julusspp., Anticarsia gemmatalis, Megascelis spp., Procornitermes spp.,Gryllotalpidae, Nezara viridula, Piezodorus spp., Acrosternum spp.,Neomegalotomus spp., Cerotoma trifurcata, Popillia japonica, Edessaspp., Liogenys fuscus, Euchistus heros, stalk borer, Scaptocoriscastanea, phyllophaga spp., Pseudoplusia includens, Spodoptera spp.,Bemisia tabaci, Agriotes spp., The compounds of the invention arepreferably used on soybean to control Diloboderus abderus, Diabroticaspeciosa, Nezara viridula, Piezodorus spp., Acrosternum spp., Cerotomatrifurcata, Popillia japonica, Euchistus heros, phyllophaga spp.,Agriotes spp.

The compounds of the invention may be used on corn to control, forexample, Euchistus heros, Dichelopsfurcatus, Diloboderus abderus,Elasmopalpus lignosellus, Spodoptera frugiperda, Nezara viridula,Cerotoma trifurcata, Popillia japonica, Agrotis ipsilon, Diabroticaspeciosa, Heteroptera, Procornitermes ssp., Scaptocoris castanea,Formicidae, Julus ssp., Dalbulus maidis, Diabrotica virgifera, Mocislatipes, Bemisia tabaci, heliothis spp., Tetranychus spp., Thrips spp.,phyllophaga spp., scaptocoris spp., Liogenysfuscus, Spodoptera spp.,Ostrinia spp., Sesamia spp., Agriotes spp. The compounds of theinvention are preferably used on corn to control Euchistus heros,Dichelops furcatus, Diloboderus abderus, Nezara viridula, Cerotomatrifurcata, Popillia japonica, Diabrotica speciosa, Diabroticavirgifera, Tetranychus spp., Thrips spp., Phyllophaga spp., Scaptocorisspp., Agriotes spp.

The compounds of the invention may be used on sugar cane to control, forexample, Sphenophorus spp., termites, Mahanarva spp. The compounds ofthe invention are preferably used on sugar cane to control termites,Mahanarva spp.

The compounds of the invention may be used on alfalfa to control, forexample, Hypera brunneipennis, Hypera postica, Colias eurytheme, Collopsspp., Empoasca solana, Epitrix, Geocoris spp., Lygus hesperus, Lyguslineolaris, Spissistilus spp., Spodoptera spp., Trichoplusia ni. Thecompounds of the invention are preferably used on alfalfa to controlHypera brunneipennis, Hypera postica, Empoasca solana, Epitrix, Lygushesperus, Lygus lineolaris, Trichoplusia ni.

The compounds of the invention may be used on brassicas to control, forexample, Plutella xylostella, Pieris spp., Mamestra spp., Plusia spp.,Trichoplusia ni, Phyllotreta spp., Spodoptera spp., Empoasca solana,Thrips spp., Spodoptera spp., Delia spp. The compounds of the inventionare preferably used on brassicas to control Plutella xylostella Pierisspp., Plusia spp., Trichoplusia ni, Phyllotreta spp., Thrips spp.

The compounds of the invention may be used on oil seed rape, e.g.canola, to control, for example, Meligethes spp., Ceutorhynchus napi,Psylloides spp.

The compounds of the invention may be used on potatoes, including sweetpotatoes, to control, for example, Empoasca spp., Leptinotarsa spp.,Diabrotica speciosa, Phthorimaea spp., Paratrioza spp., Maladeramatrida, Agriotes spp. The compounds of the invention are preferablyused on potatoes, including sweet potatoes, to control Empoasca spp.,Leptinotarsa spp., Diabrotica speciosa, Phthorimaea spp., Paratriozaspp., Agriotes spp.

The compounds of the invention may be used on cotton to control, forexample, Anthonomus grandis, Pectinophora spp., heliothis spp.,Spodoptera spp., Tetranychus spp., Empoasca spp., Thrips spp., Bemisiatabaci, Lygus spp., phyllophaga spp., Scaptocoris spp. The compounds ofthe invention are preferably used on cotton to control Anthonomusgrandis, Tetranychus spp., Empoasca spp., Thrips spp., Lygus spp.,phyllophaga spp., Scaptocoris spp.

The compounds of the invention may be used on rice to control, forexample, Leptocorisa spp., Cnaphalocrosis spp., Chilo spp., Scirpophagaspp., Lissorhoptrus spp., Oebalus pugnax. The compounds of the inventionare preferably used on rice to control Leptocorisa spp., Lissorhoptrusspp., Oebalus pugnax.

The compounds of the invention may be used on coffee to control, forexample, Hypothenemus Hampei, Perileucoptera Coffeella, Tetranychusspp., The compounds of the invention are preferably used on coffee tocontrol Hypothenemus Hampei, Perileucoptera Coffeella.

The compounds of the invention may be used on citrus to control, forexample, Panonychus citri, Phyllocoptruta oleivora, Brevipalpus spp.,Diaphorina citri, Scirtothrips spp., Thrips spp., Unaspis spp.,Ceratitis capitata, Phyllocnistis spp. The compounds of the inventionare preferably used on citrus to control Panonychus citri,Phyllocoptruta oleivora, Brevipalpus spp, Diaphorina citri, Scirtothripsspp., Thrips spp., Phyllocnistis spp.

The compounds of the invention may be used on almonds to control, forexample, Amyelois transitella, Tetranychus spp.

The compounds of the invention may be used on fruiting vegetable,including tomatoes, pepper, chili, eggplant, cucumber, squash etc, tocontrol Thrips spp, Tetranychus spp., Polyphagotarsonemus spp., Aculopsspp., Empoasca spp., Spodoptera spp., heliothis spp., Tuta absoluta,Liriomyza spp., Bemisia tabaci, Trialeurodes spp., Paratrioza spp.,Frankliniella occidentalis, Frankliniella spp., Anthonomus spp.,Phyllotreta spp., Amrasca spp., Epilachna spp., Halyomorpha spp.,Scirtothrips spp., Leucinodes spp., Neoleucinodes spp. The compounds ofthe invention are preferably used on fruiting vegetable, includingtomatoes, pepper, chili, eggplant, cucumber, squash etc, to control, forexample, Thrips spp., Tetranychus spp., Polyphagotarsonemus spp.,Aculops spp., Empoasca spp., Spodoptera spp., heliothis spp., Tutaabsoluta, Liriomyza spp., Paratrioza spp., Frankliniella occidentalis,Frankliniella spp., Amrasca spp., Scirtothrips spp., Leucinodes spp.,Neoleucinodes spp.

The compounds of the invention may be used on tea to control, forexample, Pseudaulacaspis spp., Empoasca spp., Scirtothrips spp.,Caloptilia theivora. The compounds of the invention are preferably usedon tea to control Empoasca spp., Scirtothrips spp.

The compounds of the invention may be used on bulb vegetables, includingonion, leek etc to control, for example, Thrips spp., Spodoptera spp.,heliothis spp. The compounds of the invention are preferably used onbulb vegetables, including onion, leek etc to control Thrips spp.

The compounds of the invention may be used on grapes to control, forexample, Empoasca spp., Lobesia spp., Frankliniella spp., Thrips spp.,Tetranychus spp., Rhipiphorothrips Cruentatus, EotetranychusWillamettei, Erythroneura Elegantula, Scaphoides spp. The compounds ofthe invention are preferably used on grapes to control Frankliniellaspp., Thrips spp., Tetranychus spp., Rhipiphorothrips Cruentatus,Scaphoides spp.

The compounds of the invention may be used on pome fruit, includingapples, perars etc, to control, for example, Cacopsylla spp., Psyllaspp., Panonychus ulmi, Cydia pomonella. The compounds of the inventionare preferably used on pome fruit, including apples, pears etc, tocontrol Cacopsylla spp., Psylla spp., Panonychus ulmi.

The compounds of the invention may be used on stone fruit to control,for example, Grapholita molesta, Scirtothrips spp., Thrips spp.,Frankliniella spp., Tetranychus spp. The compounds of the invention arepreferably used on stone fruit to control Scirtothrips spp., Thripsspp., Frankliniella spp., Tetranychus spp. The invention thereforeprovides a method of combating and/or controlling an animal pest, e.g.an invertebrate animal pest, which comprises applying to the pest, to alocus of the pest, or to a plant susceptible to attack by the pest apesticidally effective amount of a compound of formula (I). Inparticular, the invention provides a method of combating and/orcontrolling insects, acarines, nematodes or molluscs which comprisesapplying an insecticidally, acaricidally, nematicidally ormolluscicidally effective amount of a compound of formula (I), or acomposition containing a compound of formula (I), to a pest, a locus ofpest, preferably a plant, or to a plant susceptible to attack by a pest,The compounds of formula (I) are preferably used against insects,acarines or nematodes.

The term “plant” as used herein includes seedlings, bushes and trees.Crops are to be understood as also including those crops which have beenrendered tolerant to herbicides or classes of herbicides (e.g. ALS-,GS-, EPSPS-, PPO- and HPPD-inhibitors) by conventional methods ofbreeding or by genetic engineering. An example of a crop that has beenrendered tolerant to imidazolinones, e.g. imazamox, by conventionalmethods of breeding is Clearfield® summer rape (canola). Examples ofcrops that have been rendered tolerant to herbicides by geneticengineering methods include e.g. glyphosate- and glufosinate-resistantmaize varieties commercially available under the trade namesRoundupReady® and LibertyLink®.

Crops are also to be understood as being those which have been renderedresistant to harmful insects by genetic engineering methods, for exampleBt maize (resistant to European corn borer), Bt cotton (resistant tocotton boll weevil) and also Bt potatoes (resistant to Colorado beetle).Examples of Bt maize are the Bt 176 maize hybrids of NK® (SyngentaSeeds). Examples of transgenic plants comprising one or more genes thatcode for an insecticidal resistance and express one or more toxins areKnockOut® (maize), Yield Gard® (maize), NuCOTIN33B® (cotton), Bollgard®(cotton), NewLeaf® (potatoes), NatureGard® and Protexcta®. Plant cropsor seed material thereof can be both resistant to herbicides and, at thesame time, resistant to insect feeding (“stacked” transgenic events).For example, seed can have the ability to express an insecticidal Cry3protein while at the same time being tolerant to glyphosate.

Crops are also to be understood as being those which are obtained byconventional methods of breeding or genetic engineering and containso-called output traits (e.g. improved storage stability, highernutritional value and improved flavor).

In order to apply a compound of formula (I) as an insecticide,acaricide, nematicide or molluscicide to a pest, a locus of pest, or toa plant susceptible to attack by a pest, a compound of formula (I) isusually formulated into a composition which includes, in addition to thecompound of formula (I), a suitable inert diluent or carrier and,optionally, a surface active agent (SFA). SFAs are chemicals which areable to modify the properties of an interface (for example,liquid/solid, liquid/air or liquid/liquid interfaces) by lowering theinterfacial tension and thereby leading to changes in other properties(for example dispersion, emulsification and wetting). It is preferredthat all compositions (both solid and liquid formulations) comprise, byweight, 0.0001 to 95%, more preferably 1 to 85%, for example 5 to 60%,of a compound of formula (I). The composition is generally used for thecontrol of pests such that a compound of formula (I) is applied at arate of from 0.1 g to 10 kg per hectare, preferably from 1 g to 6 kg perhectare, more preferably from 1 g to 1 kg per hectare.

When used in a seed dressing, a compound of formula (I) is generallyused at a rate of 0.0001 g to 10 g (for example 0.001 g or 0.05 g),preferably 0.005 g to 10 g, more preferably 0.005 g to 4 g, per kilogramof seed.

In another aspect the present invention provides a compositioncomprising a pesticidally effective amount of a compound of formula (I),in particular an insecticidal, acaricidal, nematicidal or molluscicidalcomposition comprising an insecticidally, acaricidally, nematicidally ormolluscicidally effective amount of a compound of formula (I) and asuitable carrier or diluent therefor. The composition is preferably aninsecticidal, acaricidal, nematicidal or molluscicidal composition.

The compositions can be chosen from a number of formulation types,including dustable powders (DP), soluble powders (SP), water solublegranules (SG), water dispersible granules (WG), wettable powders (WP),granules (GR) (slow or fast release), soluble concentrates (SL), oilmiscible liquids (OL), ultra low volume liquids (UL), emulsifiableconcentrates (EC), dispersible concentrates (DC), emulsions (both oil inwater (EW) and water in oil (EO)), micro-emulsions (ME), suspensionconcentrates (SC), aerosols, fogging/smoke formulations, capsulesuspensions (CS) and seed treatment formulations. The formulation typechosen in any instance will depend upon the particular purpose envisagedand the physical, chemical and biological properties of the compound offormula (I).

Dustable powders (DP) may be prepared by mixing a compound of formula(I) with one or more solid diluents (for example natural clays, kaolin,pyrophyllite, bentonite, alumina, montmorillonite, kieselguhr, chalk,diatomaceous earths, calcium phosphates, calcium and magnesiumcarbonates, sulfur, lime, flours, talc and other organic and inorganicsolid carriers) and mechanically grinding the mixture to a fine powder.

Soluble powders (SP) may be prepared by mixing a compound of formula (I)with one or more water-soluble inorganic salts (such as sodiumbicarbonate, sodium carbonate or magnesium sulfate) or one or morewater-soluble organic solids (such as a polysaccharide) and, optionally,one or more wetting agents, one or more dispersing agents or a mixtureof said agents to improve water dispersibility/solubility. The mixtureis then ground to a fine powder. Similar compositions may also begranulated to form water soluble granules (SG).

Wettable powders (WP) may be prepared by mixing a compound of formula(I) with one or more solid diluents or carriers, one or more wettingagents and, preferably, one or more dispersing agents and, optionally,one or more suspending agents to facilitate the dispersion in liquids.The mixture is then ground to a fine powder. Similar compositions mayalso be granulated to form water dispersible granules (WG).

Granules (GR) may be formed either by granulating a mixture of acompound of formula (I) and one or more powdered solid diluents orcarriers, or from pre-formed blank granules by absorbing a compound offormula (I) (or a solution thereof, in a suitable agent) in a porousgranular material (such as pumice, attapulgite clays, fuller's earth,kieselguhr, diatomaceous earths or ground corn cobs) or by adsorbing acompound of formula (I) (or a solution thereof, in a suitable agent) onto a hard core material (such as sands, silicates, mineral carbonates,sulfates or phosphates) and drying if necessary. Agents which arecommonly used to aid absorption or adsorption include solvents (such asaliphatic and aromatic petroleum solvents, alcohols, ethers, ketones andesters) and sticking agents (such as polyvinyl acetates, polyvinylalcohols, dextrins, sugars and vegetable oils). One or more otheradditives may also be included in granules (for example an emulsifyingagent, wetting agent or dispersing agent).

Dispersible Concentrates (DC) may be prepared by dissolving a compoundof formula (I) in water or an organic solvent, such as a ketone, alcoholor glycol ether. These solutions may contain a surface active agent (forexample to improve water dilution or prevent crystallization in a spraytank).

Emulsifiable concentrates (EC) or oil-in-water emulsions (EW) may beprepared by dissolving a compound of formula (I) in an organic solvent(optionally containing one or more wetting agents, one or moreemulsifying agents or a mixture of said agents). Suitable organicsolvents for use in ECs include aromatic hydrocarbons (such asalkylbenzenes or alkylnaphthalenes, exemplified by SOLVESSO 100,SOLVESSO 150 and SOLVESSO 200; SOLVESSO is a Registered Trade Mark),ketones (such as cyclohexanone or methylcyclohexanone) and alcohols(such as benzyl alcohol, furfuryl alcohol or butanol),N-alkylpyrrolidones (such as N-methylpyrrolidone or N-octylpyrrolidone),dimethyl amides of fatty acids (such as C₈-C₁₀ fatty acid dimethylamide)and chlorinated hydrocarbons. An EC product may spontaneously emulsifyon addition to water, to produce an emulsion with sufficient stabilityto allow spray application through appropriate equipment. Preparation ofan EW involves obtaining a compound of formula (I) either as a liquid(if it is not a liquid at room temperature, it may be melted at areasonable temperature, typically below 70° C.) or in solution (bydissolving it in an appropriate solvent) and then emulsifiying theresultant liquid or solution into water containing one or more SFAs,under high shear, to produce an emulsion. Suitable solvents for use inEWs include vegetable oils, chlorinated hydrocarbons (such aschlorobenzenes), aromatic solvents (such as alkylbenzenes oralkylnaphthalenes) and other appropriate organic solvents which have alow solubility in water.

Microemulsions (ME) may be prepared by mixing water with a blend of oneor more solvents with one or more SFAs, to produce spontaneously athermodynamically stable isotropic liquid formulation. A compound offormula (I) is present initially in either the water or the solvent/SFAblend. Suitable solvents for use in MEs include those hereinbeforedescribed for use in ECs or in EWs. An ME may be either an oil-in-wateror a water-in-oil system (which system is present may be determined byconductivity measurements) and may be suitable for mixing water-solubleand oil-soluble pesticides in the same formulation. An ME is suitablefor dilution into water, either remaining as a microemulsion or forminga conventional oil-in-water emulsion.

Suspension concentrates (SC) may comprise aqueous or non-aqueoussuspensions of finely divided insoluble solid particles of a compound offormula (I). SCs may be prepared by ball or bead milling the solidcompound of formula (I) in a suitable medium, optionally with one ormore dispersing agents, to produce a fine particle suspension of thecompound. One or more wetting agents may be included in the compositionand a suspending agent may be included to reduce the rate at which theparticles settle. Alternatively, a compound of formula (I) may be drymilled and added to water, containing agents hereinbefore described, toproduce the desired end product.

Aerosol formulations comprise a compound of formula (I) and a suitablepropellant (for example n-butane). A compound of formula (I) may also bedissolved or dispersed in a suitable medium (for example water or awater miscible liquid, such as n-propanol) to provide compositions foruse in non-pressurized, hand-actuated spray pumps.

A compound of formula (I) may be mixed in the dry state with apyrotechnic mixture to form a composition suitable for generating, in anenclosed space, a smoke containing the compound.

Capsule suspensions (CS) may be prepared in a manner similar to thepreparation of EW formulations but with an additional polymerizationstage such that an aqueous dispersion of oil droplets is obtained, inwhich each oil droplet is encapsulated by a polymeric shell and containsa compound of formula (I) and, optionally, a carrier or diluenttherefor. The polymeric shell may be produced by either an interfacialpolycondensation reaction or by a coacervation procedure. Thecompositions may provide for controlled release of the compound offormula (I) and they may be used for seed treatment. A compound offormula (I) may also be formulated in a biodegradable polymeric matrixto provide a slow, controlled release of the compound.

A composition may include one or more additives to improve thebiological performance of the composition (for example by improvingwetting, retention or distribution on surfaces; resistance to rain ontreated surfaces; or uptake or mobility of a compound of formula (I)).Such additives include surface active agents, spray additives based onoils, for example certain mineral oils or natural plant oils (such assoy bean and rape seed oil), and blends of these with otherbio-enhancing adjuvants (ingredients which may aid or modify the actionof a compound of formula (I)).

A compound of formula (I) may also be formulated for use as a seedtreatment, for example as a powder composition, including a powder fordry seed treatment (DS), a water soluble powder (SS) or a waterdispersible powder for slurry treatment (WS), or as a liquidcomposition, including a flowable concentrate (FS), a solution (LS) or acapsule suspension (CS). The preparations of DS, SS, WS, FS and LScompositions are very similar to those of, respectively, DP, SP, WP, SCand DC compositions described above. Compositions for treating seed mayinclude an agent for assisting the adhesion of the composition to theseed (for example a mineral oil or a film-forming barrier).

Wetting agents, dispersing agents and emulsifying agents may be surfaceSFAs of the cationic, anionic, amphoteric or non-ionic type.

Suitable SFAs of the cationic type include quaternary ammonium compounds(for example cetyltrimethyl ammonium bromide), imidazolines and aminesalts.

Suitable anionic SFAs include alkali metals salts of fatty acids, saltsof aliphatic monoesters of sulfuric acid (for example sodium laurylsulfate), salts of sulfonated aromatic compounds (for example sodiumdodecylbenzenesulfonate, calcium dodecylbenzenesulfonate,butylnaphthalene sulfonate and mixtures of sodium di-isopropyl- andtri-isopropyl-naphthalene sulfonates), ether sulfates, alcohol ethersulfates (for example sodium laureth-3-sulfate), ether carboxylates (forexample sodium laureth-3-carboxylate), phosphate esters (products fromthe reaction between one or more fatty alcohols and phosphoric acid(predominately mono-esters) or phosphorus pentoxide (predominatelydi-esters), for example the reaction between lauryl alcohol andtetraphosphoric acid; additionally these products may be ethoxylated),sulfosuccinamates, paraffin or olefine sulfonates, taurates andlignosulfonates.

Suitable SFAs of the amphoteric type include betaines, propionates andglycinates.

Suitable SFAs of the non-ionic type include condensation products ofalkylene oxides, such as ethylene oxide, propylene oxide, butylene oxideor mixtures thereof, with fatty alcohols (such as oleyl alcohol or cetylalcohol) or with alkylphenols (such as octylphenol, nonylphenol oroctylcresol); partial esters derived from long chain fatty acids orhexitol anhydrides; condensation products of said partial esters withethylene oxide; block polymers (comprising ethylene oxide and propyleneoxide); alkanolamides; simple esters (for example fatty acidpolyethylene glycol esters); amine oxides (for example lauryl dimethylamine oxide); and lecithins.

Suitable suspending agents include hydrophilic colloids (such aspolysaccharides, polyvinylpyrrolidone or sodium carboxymethylcellulose)and swelling clays (such as bentonite or attapulgite).

A compound of formula (I) may be applied by any of the known means ofapplying pesticidal compounds. For example, it may be applied,formulated or unformulated, to the pests or to a locus of the pests(such as a habitat of the pests, or a growing plant liable toinfestation by the pests) or to any part of the plant, including thefoliage, stems, branches or roots, to the seed before it is planted orto other media in which plants are growing or are to be planted (such assoil surrounding the roots, the soil generally, paddy water orhydroponic culture systems), directly or it may be sprayed on, dustedon, applied by dipping, applied as a cream or paste formulation, appliedas a vapor or applied through distribution or incorporation of acomposition (such as a granular composition or a composition packed in awater-soluble bag) in soil or an aqueous environment.

A compound of formula (I) may also be injected into plants or sprayedonto vegetation using electrodynamic spraying techniques or other lowvolume methods, or applied by land or aerial irrigation systems.

Compositions for use as aqueous preparations (aqueous solutions ordispersions) are generally supplied in the form of a concentratecontaining a high proportion of the active ingredient, the concentratebeing added to water before use. These concentrates, which may includeDCs, SCs, ECs, EWs, MEs, SGs, SPs, WPs, WGs and CSs, are often requiredto withstand storage for prolonged periods and, after such storage, tobe capable of addition to water to form aqueous preparations whichremain homogeneous for a sufficient time to enable them to be applied byconventional spray equipment. Such aqueous preparations may containvarying amounts of a compound of formula (I) (for example 0.0001 to 10%,by weight) depending upon the purpose for which they are to be used.

A compound of formula (I) may be used in mixtures with fertilizers (forexample nitrogen-, potassium- or phosphorus-containing fertilizers).Suitable formulation types include granules of fertilizer. The mixturespreferably contain up to 25% by weight of the compound of formula (I).

The invention therefore also provides a fertilizer compositioncomprising a fertilizer and a compound of formula (I).

The compositions of this invention may contain other compounds havingbiological activity, for example micronutrients or compounds havingfungicidal activity or which possess plant growth regulating,herbicidal, insecticidal, nematicidal or acaricidal activity.

The compound of formula (I) may be the sole active ingredient of thecomposition or it may be admixed with one or more additional activeingredients such as a pesticide, e.g. a insecticide, fungicide orherbicide, or a synergist or plant growth regulator where appropriate.An additional active ingredient may provide a composition having abroader spectrum of activity or increased persistence at a locus;synergize the activity or complement the activity (for example byincreasing the speed of effect or overcoming repellency) of the compoundof formula (I); or help to overcome or prevent the development ofresistance to individual components. The particular additional activeingredient will depend upon the intended utility of the composition.

The compounds of the invention are also useful in the field of animalhealth, e.g. they may be used against parasitic invertebrate pests, morepreferably against parasitic invertebrate pests in or on an animal.Examples of pests include nematodes, trematodes, cestodes, flies, mites,tricks, lice, fleas, true bugs and maggots. The animal may be anon-human animal, e.g. an animal associated with agriculture, e.g. acow, a pig, a sheep, a goat, a horse, or a donkey, or a companionanimal, e.g. a dog or a cat.

In a further aspect the invention provides a compound of the inventionfor use in a method of therapeutic treatment.

In a further aspect the invention relates to a method of controllingparasitic invertebrate pests in or on an animal comprising administeringa pesticidally effective amount of a compound of the invention. Theadministration may be for example oral administration, parenteraladministration or external administration, e.g. to the surface of theanimal body. In a further aspect the invention relates to a compound ofthe invention for controlling parasitic invertebrate pests in or on ananimal. In a further aspect the invention relates to use of a compoundof the invention in the manufacture of a medicament for controllingparasitic invertebrate pests in or on an animal

In a further aspect, the invention relates to a method of controllingparasitic invertebrate pests comprising administering a pesticidallyeffective amount of a compound of the invention to the environment inwhich an animal resides.

In a further aspect the invention relates to a method of protecting ananimal from a parasitic invertebrate pest comprising administering tothe animal a pesticidally effective amount of a compound of theinvention. In a further aspect the invention relates to a compound ofthe invention for use in protecting an animal from a parasiticinvertebrate pest. In a further aspect the invention relates to use of acompound of the invention in the manufacture of a medicament forprotecting an animal from a parasitic invertebrate pest.

In a further aspect the invention provides a method of treating ananimal suffering from a parasitic invertebrate pest comprisingadministering to the animal a pesticidally effective amount of acompound of the invention. In a further aspect the invention relates toa compound of the invention for use in treating an animal suffering froma parasitic invertebrate pest. In a further aspect the invention relatesto use of a compound of the invention in the manufacture of a medicamentfor treating an animal suffering from a parasitic invertebrate pest.

In a further aspect, the invention provides a pharmaceutical compositioncomprising a compound of the invention and a pharmaceutically suitableexcipient.

The compounds of the invention may be used alone or in combination withone or more other biologically active ingredients.

In one aspect the invention provides a combination product comprising apesticidally effective amount of a component A and a pesticidallyeffective amount of component B wherein component A is a compound of theinvention and component B is a compound as described below.

The compounds of the invention may be used in combination withanthelmintic agents. Such anthelmintic agents include, compoundsselected from the macrocyclic lactone class of compounds such asivermectin, avermectin, abamectin, emamectin, eprinomectin, doramectin,selamectin, moxidectin, nemadectin and milbemycin derivatives asdescribed in EP-357460, EP-444964 and EP-594291. Additional anthelminticagents include semisynthetic and biosynthetic avermectin/milbemycinderivatives such as those described in U.S. Pat. No. 5,015,630,WO-9415944 and WO-9522552. Additional anthelmintic agents include thebenzimidazoles such as albendazole, cambendazole, fenbendazole,flubendazole, mebendazole, oxfendazole, oxibendazole, parbendazole, andother members of the class. Additional anthelmintic agents includeimidazothiazoles and tetrahydropyrimidines such as tetramisole,levamisole, pyrantel pamoate, oxantel or morantel. Additionalanthelmintic agents include flukicides, such as triclabendazole andclorsulon and the cestocides, such as praziquantel and epsiprantel.

The compounds of the invention may be used in combination withderivatives and analogues of the paraherquamide/marcfortine class ofanthelmintic agents, as well as the antiparasitic oxazolines such asthose disclosed in U.S. Pat. No. 5,478,855, U.S. Pat. No. 4,639,771 andDE-19520936.

The compounds of the invention may be used in combination withderivatives and analogues of the general class of dioxomorpholineantiparasitic agents as described in WO-9615121 and also withanthelmintic active cyclic depsipeptides such as those described inWO-9611945, WO-9319053, WO-9325543, EP-626375, EP-382173, WO-9419334,EP-382173, and EP-503538.

The compounds of the invention may be used in combination with otherectoparasiticides; for example, fipronil; pyrethroids; organophosphates;insect growth regulators such as lufenuron; ecdysone agonists such astebufenozide and the like; neonicotinoids such as imidacloprid and thelike.

The compounds of the invention may be used in combination with terpenealkaloids, for example those described in International PatentApplication Publication Numbers WO95/19363 or WO04/72086, particularlythe compounds disclosed therein.

Other examples of such biologically active compounds that the compoundsof the invention may be used in combination with include but are notrestricted to the following: Organophosphates: acephate, azamethiphos,azinphos-ethyl, azinphos-methyl, bromophos, bromophos-ethyl, cadusafos,chlorethoxyphos, chlorpyrifos, chlorfenvinphos, chlormephos, demeton,demeton-S-methyl, demeton-S-methyl sulphone, dialifos, diazinon,dichlorvos, dicrotophos, dimethoate, disulfoton, ethion, ethoprophos,etrimfos, famphur, fenamiphos, fenitrothion, fensulfothion, fenthion,flupyrazofos, fonofos, formothion, fosthiazate, heptenophos, isazophos,isothioate, isoxathion, malathion, methacriphos, methamidophos,methidathion, methyl-parathion, mevinphos, monocrotophos, naled,omethoate, oxydemeton-methyl, paraoxon, parathion, parathion-methyl,phenthoate, phosalone, phosfolan, phosphocarb, phosmet, phosphamidon,phorate, phoxim, pirimiphos, pirimiphos-methyl, profenofos, propaphos,proetamphos, prothiofos, pyraclofos, pyridapenthion, quinalphos,sulprophos, temephos, terbufos, tebupirimfos, tetrachlorvinphos,thimeton, triazophos, trichlorfon, vamidothion.

Carbamates: alanycarb, aldicarb, 2-sec-butylphenyl methylcarbamate,benfuracarb, carbaryl, carbofuran, carbosulfan, cloethocarb,ethiofencarb, fenoxycarb, fenthiocarb, furathiocarb, HCN-801,isoprocarb, indoxacarb, methiocarb, methomyl,5-methyl-m-cumenylbutyryl(methyl)carbamate, oxamyl, pirimicarb,propoxur, thiodicarb, thiofanox, triazamate, UC-51717.

Pyrethroids: acrinathin, allethrin, alphametrin, 5-benzyl-3-furylmethyl(E)-(1R)-cis-2,2-dimethyl-3-(2-oxothiolan-3-ylidenemethyl)cyclopropanecarboxylate,bifenthrin, beta-cyfluthrin, cyfluthrin, a-cypermethrin,beta-cypermethrin, bioallethrin, bioallethrin((S)-cyclopentylisomer),bioresmethrin, bifenthrin, NCI-85193, cycloprothrin, cyhalothrin,cythithrin, cyphenothrin, deltamethrin, empenthrin, esfenvalerate,ethofenprox, fenfluthrin, fenpropathrin, fenvalerate, flucythrinate,flumethrin, fluvalinate (D isomer), imiprothrin, cyhalothrin,lambda-cyhalothrin, permethrin, phenothrin, prallethrin, pyrethrins(natural products), resmethrin, tetramethrin, transfluthrin,theta-cypermethrin, silafluofen, t-fluvalinate, tefluthrin,tralomethrin, Zeta-cypermethrin.

Arthropod growth regulators: a) chitin synthesis inhibitors:benzoylureas: chlorfluazuron, diflubenzuron, fluazuron, flucycloxuron,flufenoxuron, hexaflumuron, lufenuron, novaluron, teflubenzuron,triflumuron, buprofezin, diofenolan, hexythiazox, etoxazole,chlorfentazine; b) ecdysone antagonists: halofenozide, methoxyfenozide,tebufenozide; c) juvenoids: pyriproxyfen, methoprene (includingS-methoprene), fenoxycarb; d) lipid biosynthesis inhibitors:spirodiclofen.

Other antiparasitics: acequinocyl, amitraz, AKD-1022, ANS-118,azadirachtin, Bacillus thuringiensis, bensultap, bifenazate, binapacryl,bromopropylate, BTG-504, BTG-505, camphechlor, cartap, chlorobenzilate,chlordimeform, chlorfenapyr, chromafenozide, clothianidine, cyromazine,diacloden, diafenthiuron, DBI-3204, dinactin,dihydroxymethyldihydroxypyrrolidine, dinobuton, dinocap, endosulfan,ethiprole, ethofenprox, fenazaquin, flumite, MTI-800, fenpyroximate,fluacrypyrim, flubenzimine, flubrocythrinate, flufenzine, flufenprox,fluproxyfen, halofenprox, hydramethylnon, IKI-220, kanemite, NC-196,neem guard, nidinorterfuran, nitenpyram, SD-35651, WL-108477, pirydaryl,propargite, protrifenbute, pymethrozine, pyridaben, pyrimidifen,NC-1111, R-195, RH-0345, RH-2485, RYI-210, S-1283, S-1833, SI-8601,silafluofen, silomadine, spinosad, tebufenpyrad, tetradifon,tetranactin, thiacloprid, thiocyclam, thiamethoxam, tolfenpyrad,triazamate, triethoxyspinosyn, trinactin, verbutin, vertalec, YI-5301.

Fungicides: acibenzolar, aldimorph, ampropylfos, andoprim, azaconazole,azoxystrobin, benalaxyl, benomyl, bialaphos, blasticidin-S, Bordeauxmixture, bromuconazole, bupirimate, carpropamid, captafol, captan,carbendazim, chlorfenazole, chloroneb, chloropicrin, chlorothalonil,chlozolinate, copper oxychloride, copper salts, cyflufenamid, cymoxanil,cyproconazole, cyprodinil, cyprofuram, RH-7281, diclocymet,diclobutrazole, diclomezine, dicloran, difenoconazole, RP-407213,dimethomorph, domoxystrobin, diniconazole, diniconazole-M, dodine,edifenphos, epoxiconazole, famoxadone, fenamidone, fenarimol,fenbuconazole, fencaramid, fenpiclonil, fenpropidin, fenpropimorph,fentin acetate, fluazinam, fludioxonil, flumetover, flumorf/flumorlin,fentin hydroxide, fluoxastrobin, fluquinconazole, flusilazole,flutolanil, flutriafol, folpet, fosetyl-aluminium, furalaxyl,furametapyr, hexaconazole, ipconazole, iprobenfos, iprodione,isoprothiolane, kasugamycin, krsoxim-methyl, mancozeb, maneb, mefenoxam,mepronil, metalaxyl, metconazole, metominostrobin/fenominostrobin,metrafenone, myclobutanil, neo-asozin, nicobifen, orysastrobin,oxadixyl, penconazole, pencycuron, probenazole, prochloraz, propamocarb,propioconazole, proquinazid, prothioconazole, pyrifenox, pyraclostrobin,pyrimethanil, pyroquilon, quinoxyfen, spiroxamine, sulfur, tebuconazole,tetrconazole, thiabendazole, thifluzamide, thiophanate-methyl, thiram,tiadinil, triadimefon, triadimenol, tricyclazole, trifloxystrobin,triticonazole, validamycin, vinclozin.

Biological agents: Bacillus thuringiensis ssp aizawai, kurstaki,Bacillus thuringiensis delta endotoxin, baculovirus, entomopathogenicbacteria, virus and fungi.

Bactericides: chlortetracycline, oxytetracycline, streptomycin.

Other biological agents: enrofloxacin, febantel, penethamate, moloxicam,cefalexin, kanamycin, pimobendan, clenbuterol, omeprazole, tiamulin,benazepril, pyriprole, cefquinome, florfenicol, buserelin, cefovecin,tulathromycin, ceftiour, carprofen, metaflumizone, praziquarantel,triclabendazole.

When used in combination with other active ingredients, the compounds ofthe invention are preferably used in combination with the following(where “Tx” means a compound of formula (I), and in particular onespecific compound selected from the Table 1 (compounds 1.1 to 1.112) ora specific compound selected from the Table 2 (compounds 2.1 to 2.112)or a specific compound selected from Table A (compounds 1 to 5), whichmay result in a synergistic combination with the given activeingredient): imidacloprid+Tx, enrofloxacin+Tx, praziquantel+Tx, pyrantelembonate+Tx, febantel+Tx, penethamate+Tx, moloxicam+Tx, cefalexin+Tx,kanamycin+Tx, pimobendan+Tx, clenbuterol+Tx, fipronil+Tx, ivermectin+Tx,omeprazole+Tx, tiamulin+Tx, benazepril+Tx, milbemycin+Tx, cyromazine+Tx,thiamethoxam+Tx, pyriprole+Tx, deltamethrin+Tx, cefquinome+Tx,florfenicol+Tx, buserelin+Tx, cefovecin+Tx, tulathromycin+Tx,ceftiour+Tx, selamectin+Tx, carprofen+Tx, metaflumizone+Tx,moxidectin+Tx, methoprene (including S-methoprene)+Tx, clorsulon+Tx,pyrantel+Tx, amitraz+Tx, triclabendazole+Tx, avermectin+Tx,abamectin+Tx, emamectin+Tx, eprinomectin+Tx, doramectin+Tx,selamectin+Tx, nemadectin+Tx, albendazole+Tx, cambendazole+Tx,fenbendazole+Tx, flubendazole+Tx, mebendazole+Tx, oxfendazole+Tx,oxibendazole+Tx, parbendazole+Tx, tetramisole+Tx, levamisole+Tx,pyrantel pamoate+Tx, oxantel+Tx, morantel+Tx, triclabendazole+Tx,epsiprantel+Tx, fipronil+Tx, lufenuron+Tx, ecdysone+Tx ortebufenozide+Tx; more preferably, enrofloxacin+Tx, praziquantel+Tx,pyrantel embonate+Tx, febantel+Tx, penethamate+Tx, moloxicam+Tx,cefalexin+Tx, kanamycin+Tx, pimobendan+Tx, clenbuterol+Tx,omeprazole+Tx, tiamulin+Tx, benazepril+Tx, pyriprole+Tx, cefquinome+Tx,florfenicol+Tx, buserelin+Tx, cefovecin+Tx, tulathromycin+Tx,ceftiour+Tx, selamectin+Tx, carprofen+Tx, moxidectin+Tx, clorsulon+Tx,pyrantel+Tx, eprinomectin+Tx, doramectin+Tx, selamectin+Tx,nemadectin+Tx, albendazole+Tx, cambendazole+Tx, fenbendazole+Tx,flubendazole+Tx, mebendazole+Tx, oxfendazole+Tx, oxibendazole+Tx,parbendazole+Tx, tetramisole+Tx, levamisole+Tx, pyrantel pamoate+Tx,oxantel+Tx, morantel+Tx, triclabendazole+Tx, epsiprantel+Tx,lufenuron+Tx or ecdysone+Tx; even more preferably enrofloxacin+Tx,praziquantel+Tx, pyrantel embonate+Tx, febantel+Tx, penethamate+Tx,moloxicam+Tx, cefalexin+Tx, kanamycin+Tx, pimobendan+Tx, clenbuterol+Tx,omeprazole+Tx, tiamulin+Tx, benazepril+Tx, pyriprole+Tx, cefquinome+Tx,florfenicol+Tx, buserelin+Tx, cefovecin+Tx, tulathromycin+Tx,ceftiour+Tx, selamectin+Tx, carprofen+Tx, moxidectin+Tx, clorsulon+Tx orpyrantel+Tx.

Examples of ratios include 100:1 to 1:6000, 50:1 to 1:50, 20:1 to 1:20,even more especially from 10:1 to 1:10, 5:1 to 1:5, 2:1 to 1:2, 4:1 to2:1, 1:1, or 5:1, or 5:2, or 5:3, or 5:4, or 4:1, or 4:2, or 4:3, or3:1, or 3:2, or 2:1, or 1:5, or 2:5, or 3:5, or 4:5, or 1:4, or 2:4, or3:4, or 1:3, or 2:3, or 1:2, or 1:600, or 1:300, or 1:150, or 1:35, or2:35, or 4:35, or 1:75, or 2:75, or 4:75, or 1:6000, or 1:3000, or1:1500, or 1:350, or 2:350, or 4:350, or 1:750, or 2:750, or 4:750.Those mixing ratios are understood to include, on the one hand, ratiosby weight and also, on the other hand, molar ratios.

Of particular note is a combination where the additional activeingredient has a different site of action from the compound of formulaI. In certain instances, a combination with at least one other parasiticinvertebrate pest control active ingredient having a similar spectrum ofcontrol but a different site of action will be particularly advantageousfor resistance management. Thus, a combination product of the inventionmay comprise a pesticidally effective amount of a compound of formula Iand pesticidally effective amount of at least one additional parasiticinvertebrate pest control active ingredient having a similar spectrum ofcontrol but a different site of action.

One skilled in the art recognizes that because in the environment andunder physiological conditions salts of chemical compounds are inequilibrium with their corresponding non salt forms, salts share thebiological utility of the non salt forms.

Thus a wide variety of salts of compounds of the invention (and activeingredients used in combination with the active ingredients of theinvention) may be useful for control of invertebrate pests and animalparasites. Salts include acid-addition salts with inorganic or organicacids such as hydrobromic, hydrochloric, nitric, phosphoric, sulfuric,acetic, butyric, fumaric, lactic, maleic, malonic, oxalic, propionic,salicylic, tartaric, 4-toluenesulfonic or valeric acids. The compoundsof the invention also include N-oxides. Accordingly, the inventioncomprises combinations of compounds of the invention including N-oxidesand salts thereof and an additional active ingredient including N-oxidesand salts thereof.

The compositions for use in animal health may also contain formulationauxiliaries and additives, known to those skilled in the art asformulation aids (some of which may be considered to also function assolid diluents, liquid diluents or surfactants). Such formulationauxiliaries and additives may control: pH (buffers), foaming duringprocessing (antifoams such polyorganosiloxanes), sedimentation of activeingredients (suspending agents), viscosity (thixotropic thickeners),in-container microbial growth (antimicrobials), product freezing(antifreezes), color (dyes/pigment dispersions), wash-off (film formersor stickers), evaporation (evaporation retardants), and otherformulation attributes. Film formers include, for example, polyvinylacetates, polyvinyl acetate copolymers, polyvinylpyrrolidone-vinylacetate copolymer, polyvinyl alcohols, polyvinyl alcohol copolymers andwaxes. Examples of formulation auxiliaries and additives include thoselisted in McCutcheon's Volume 2: Functional Materials, annualInternational and North American editions published by McCutcheon'sDivision, The Manufacturing Confectioner Publishing Co.; and PCTPublication WO 03/024222.

The compounds of the invention can be applied without other adjuvants,but most often application will be of a formulation comprising one ormore active ingredients with suitable carriers, diluents, andsurfactants and possibly in combination with a food depending on thecontemplated end use. One method of application involves spraying awater dispersion or refined oil solution of the combination products.Compositions with spray oils, spray oil concentrations, spreaderstickers, adjuvants, other solvents, and synergists such as piperonylbutoxide often enhance compound efficacy. Such sprays can be appliedfrom spray containers such as a can, a bottle or other container, eitherby means of a pump or by releasing it from a pressurized container,e.g., a pressurized aerosol spray can. Such spray compositions can takevarious forms, for example, sprays, mists, foams, fumes or fog. Suchspray compositions thus can further comprise propellants, foamingagents, etc. as the case may be. Of note is a spray compositioncomprising a pesticidally effective amount of a compound of theinvention and a carrier. One embodiment of such a spray compositioncomprises a pesticidally effective amount of a compound of the inventionand a propellant. Representative propellants include, but are notlimited to, methane, ethane, propane, butane, isobutane, butene,pentane, isopentane, neopentane, pentene, hydrofluorocarbons,chlorofluorocarbons, dimethyl ether, and mixtures of the foregoing. Ofnote is a spray composition (and a method utilizing such a spraycomposition dispensed from a spray container) used to control at leastone parasitic invertebrate pest selected from the group consisting ofmosquitoes, black flies, stable flies, deer flies, horse flies, wasps,yellow jackets, hornets, ticks, spiders, ants, gnats, and the like,including individually or in combinations.

The controlling of animal parasites includes controlling externalparasites that are parasitic to the surface of the body of the hostanimal (e.g., shoulders, armpits, abdomen, inner part of the thighs) andinternal parasites that are parasitic to the inside of the body of thehost animal (e.g., stomach, intestine, lung, veins, under the skin,lymphatic tissue). External parasitic or disease transmitting pestsinclude, for example, chiggers, ticks, lice, mosquitoes, flies, mitesand fleas. Internal parasites include heartworms, hookworms andhelminths. The compounds of the invention may be particularly suitablefor combating external parasitic pests. The compounds of the inventionmay be suitable for systemic and/or non-systemic control of infestationor infection by parasites on animals.

The compounds of the invention may be suitable for combating parasiticinvertebrate pests that infest animal subjects including those in thewild, livestock and agricultural working animals. Livestock is the termused to refer (singularly or plurally) to a domesticated animalintentionally reared in an agricultural setting to make produce such asfood or fiber, or for its labor; examples of livestock include cattle,sheep, goats, horses, pigs, donkeys, camels, buffalo, rabbits, hens,turkeys, ducks and geese (e.g., raised for meat, milk, butter, eggs,fur, leather, feathers and/or wool). By combating parasites, fatalitiesand performance reduction (in terms of meat, milk, wool, skins, eggs,etc.) are reduced, so that applying the compounds of the inventionallows more economic and simple husbandry of animals.

The compounds of the invention may be suitable for combating parasiticinvertebrate pests that infest companion animals and pets (e.g., dogs,cats, pet birds and aquarium fish), research and experimental animals(e.g., hamsters, guinea pigs, rats and mice), as well as animals raisedfor/in zoos, wild habitats and/or circuses.

In an embodiment of this invention, the animal is preferably avertebrate, and more preferably a mammal, avian or fish. In a particularembodiment, the animal subject is a mammal (including great apes, suchas humans). Other mammalian subjects include primates (e.g., monkeys),bovine (e.g., cattle or dairy cows), porcine (e.g., hogs or pigs), ovine(e.g., goats or sheep), equine (e.g., horses), canine (e.g., dogs),feline (e.g., house cats), camels, deer, donkeys, buffalos, antelopes,rabbits, and rodents (e.g., guinea pigs, squirrels, rats, mice, gerbils,and hamsters). Avians include Anatidae (swans, ducks and geese),Columbidae (e.g., doves and pigeons), Phasianidae (e.g., partridges,grouse and turkeys), Thesienidae (e.g., domestic chickens), Psittacines(e.g., parakeets, macaws, and parrots), game birds, and ratites (e.g.,ostriches).

Birds treated or protected by the compounds of the invention can beassociated with either commercial or noncommercial aviculture. Theseinclude Anatidae, such as swans, geese, and ducks, Columbidae, such asdoves and domestic pigeons, Phasianidae, such as partridge, grouse andturkeys, Thesienidae, such as domestic chickens, and Psittacines, suchas parakeets, macaws and parrots raised for the pet or collector market,among others.

For purposes of the present invention, the term “fish” is understood toinclude without limitation, the Teleosti grouping of fish, i.e.,teleosts. Both the Salmoniformes order (which includes the Salmonidaefamily) and the Perciformes order (which includes the Centrarchidaefamily) are contained within the Teleosti grouping. Examples ofpotential fish recipients include the Salmonidae, Serranidae, Sparidae,Cichlidae, and Centrarchidae, among others.

Other animals are also contemplated to benefit from the inventivemethods, including marsupials (such as kangaroos), reptiles (such asfarmed turtles), and other economically important domestic animals forwhich the inventive methods are safe and effective in treating orpreventing parasite infection or infestation.

Examples of parasitic invertebrate pests controlled by administering apesticidally effective amount of the compounds of the invention to ananimal to be protected include ectoparasites (arthropods, acarines,etc.) and endoparasites (helminths, e.g., nematodes, trematodes,cestodes, acanthocephalans, etc.).

The disease or group of diseases described generally as helminthiasis isdue to infection of an animal host with parasitic worms known ashelminths. The term ‘helminths’ is meant to include nematodes,trematodes, cestodes and acanthocephalans. Helminthiasis is a prevalentand serious economic problem with domesticated animals such as swine,sheep, horses, cattle, goats, dogs, cats and poultry.

Among the helminths, the group of worms described as nematodes causeswidespread and at times serious infection in various species of animals.

Nematodes that are contemplated to be treated by the compounds of theinvention include, without limitation, the following genera:Acanthocheilonema, Aelurostrongylus, Ancylostoma, Angiostrongylus,Ascaridia, Ascaris, Brugia, Bunostomum, Capillaria, Chabertia, Cooperia,Crenosoma, Dictyocaulus, Dioctophyme, Dipetalonema, Diphyllobothrium,Dirofilaria, Dracunculus, Enterobius, Filaroides, Haemonchus, Heterakis,Lagochilascaris, Loa, Mansonella, Muellerius, Necator, Nematodirus,Oesophagostomum, Ostertagia, Oxyuris, Parafilaria, Parascaris,Physaloptera, Protostrongylus, Setaria, Spirocerca, Stephanofilaria,Strongyloides, Strongylus, Thelazia, Toxascaris, Toxocara, Trichinella,Trichonema, Trichostrongylus, Trichuris, Uncinaria and Wuchereria.

Of the above, the most common genera of nematodes infecting the animalsreferred to above are Haemonchus, Trichostrongylus, Ostertagia,Nematodirus, Cooperia, Ascaris, Bunostomum, Oesophagostomum, Chabertia,Trichuris, Strongylus, Trichonema, Dictyocaulus, Capillaria, Heterakis,Toxocara, Ascaridia, Oxyuris, Ancylostoma, Uncinaria, Toxascaris andParascaris. Certain of these, such as Nematodirus, Cooperia andOesophagostomum attack primarily the intestinal tract while others, suchas Haemonchus and Ostertagia, are more prevalent in the stomach whileothers such as Dictyocaulus are found in the lungs. Still otherparasites may be located in other tissues such as the heart and bloodvessels, subcutaneous and lymphatic tissue and the like.

Trematodes that are contemplated to be treated by the invention and bythe inventive methods include, without limitation, the following genera:Alaria, Fasciola, Nanophyetus, Opisthorchis, Paragonimus andSchistosoma.

Cestodes that are contemplated to be treated by the invention and by theinventive methods include, without limitation, the following genera:Diphyllobothrium, Diplydium, Spirometra and Taenia.

The most common genera of parasites of the gastrointestinal tract ofhumans are

Ancylostoma, Necator, Ascaris, Strongy hides, Trichinella, Capillaria,Trichuris and Enterobius. Other medically important genera of parasiteswhich are found in the blood or other tissues and organs outside thegastrointestinal tract are the filarial worms such as Wuchereria,Brugia, Onchocerca and Loa, as well as Dracunculus and extra intestinalstages of the intestinal worms Strongyloides and Trichinella.

Numerous other helminth genera and species are known to the art, and arealso contemplated to be treated by the compounds of the invention. Theseare enumerated in great detail in Textbook of Veterinary ClinicalParasitology, Volume 1, Helminths, E. J. L. Soulsby, F. A. Davis Co.,Philadelphia, Pa.; Helminths, Arthropods and Protozoa, (6^(th) Editionof Monnig's Veterinary Helminthology and Entomology), E. J. L. Soulsby,Williams and Wilkins Co., Baltimore, Md.

The compounds of the invention may be effective against a number ofanimal ectoparasites (e.g., arthropod ectoparasites of mammals andbirds).

Insect and acarine pests include, e.g., biting insects such as flies andmosquitoes, mites, ticks, lice, fleas, true bugs, parasitic maggots, andthe like.

Adult flies include, e.g., the horn fly or Haematobia irritans, thehorse fly or Tabanus spp., the stable fly or Stomoxys calcitrans, theblack fly or Simulium spp., the deer fly or Chrysops spp., the louse flyor Melophagus ovinus, and the tsetse fly or Glossina spp. Parasitic flymaggots include, e.g., the bot fly (Oestrus ovis and Cuterebra spp.),the blow fly or Phaenicia spp., the screwworm or Cochliomyiahominivorax, the cattle grub or Hypoderma spp., the fleeceworm and theGastrophilus of horses. Mosquitoes include, for example, Culex spp.,Anopheles spp., and Aedes spp.

Mites include Mesostigmalphatalpha spp., e.g., mesostigmatids such asthe chicken mite, Dermalphanyssus galphallinalphae; itch or scab mitessuch as Sarcoptidae spp., for example, Salpharcoptes scalphabiei; mangemites such as Psoroptidae spp., including Chorioptes bovis and Psoroptesovis; chiggers e.g., Trombiculidae spp., for example the North Americanchigger, Trombiculalpha alphalfreddugesi.

Ticks include, e.g., soft-bodied ticks including Argasidae spp., forexample Argalphas spp., and Ornithodoros spp.; hard-bodied ticksincluding Ixodidae spp., for example Rhipicephalphalus sanguineus,Dermacentor variabilis, Dermacentor andersoni, Amblyomma americanum,Ixodes scapularis and other Rhipicephalus spp., (including the formerBoophilus genera).

Lice include, e.g., sucking lice, e.g., Menopon spp.

and Bovicola spp.; biting lice, e.g., Haematopinus spp., Linognathusspp., and Solenopotes spp.

Fleas include, e.g., Ctenocephalides spp., such as dog flea(Ctenocephalides canis) and cat flea (Ctenocephalides felis); Xenopsyllaspp., such as oriental rat flea (Xenopsylla cheopis); and Pulex spp.,such as human flea (Pulex irritans).

True bugs include, e.g., Cimicidae or e.g., the common bed bug (Cimexlectularius); Triatominae spp., including triatomid bugs also known askissing bugs; for example Rhodnius prolixus and Triatoma spp.

Generally, flies, fleas, lice, mosquitoes, gnats, mites, ticks andhelminths cause tremendous losses to the livestock and companion animalsectors. Arthropod parasites also are a nuisance to humans and canvector disease-causing organisms in humans and animals.

Numerous other parasitic invertebrate pests are known to the art, andare also contemplated to be treated by the compounds of the invention.These are enumerated in great detail in Medical and VeterinaryEntomology, D. S. Kettle, John Wiley AND Sons, New York and Toronto;Control of Arthropod Pests of Livestock: A Review of Technology, R. O.Drummand, J. E. George, and S. E. Kunz, CRC Press, Boca Raton, Fla.

The compounds of the invention may also be effective againstectoparasites including: flies such as Haematobia (Lyperosia) irritans(horn fly), Simulium spp., (blackfly), Glossina spp., (tsetse flies),Hydrotaea irritans (head fly), Musca autumnalis (face fly), Muscadomestica (house fly), Morellia simplex (sweat fly), Tabanus spp.,(horse fly), Hypoderma bovis, Hypoderma lineatum, Lucilia sericata,Lucilia cuprina (green blowfly), Calliphora spp., (blowfly),Protophormia spp., Oestrus ovis (nasal botfly), Culicoides spp.,(midges), Hippobosca equine, Gastrophilus intestinalis, Gastrophilushaemorrhoidalis and Gastrophilus nasalis; lice such as Bovicola(Damalinia) bovis, Bovicola equi, Haematopinus asini, Felicolasubrostratus, Heterodoxus spiniger, Lignonathus setosus and Trichodectescanis; keds such as Melophagus ovinus; and mites such as Psoroptes spp.,Sarcoptes scabei, Chorioptes bovis, Demodex equi, Cheyletiella spp.,Notoedres cati, Trombicula spp., and Otodectes cyanotis (ear mites).

Treatments of the invention are by conventional means such as by enteraladministration in the form of, for example, tablets, capsules, drinks,drenching preparations, granulates, pastes, boli, feed-throughprocedures, or suppositories; or by parenteral administration, such as,for example, by injection (including intramuscular, subcutaneous,intravenous, intraperitoneal) or implants; or by nasal administration.

When compounds of the invention are applied in combination with anadditional biologically active ingredient, they may be administeredseparately e.g. as separate compositions. In this case, the biologicallyactive ingredients may be administered simultaneously or sequentially.Alternatively, the biologically active ingredients may be components ofone composition.

The compounds of the invention may be administered in a controlledrelease form, for example in subcutaneous or orally adminstered slowrelease formulations.

Typically a parasiticidal composition according to the present inventioncomprises a compound of the invention, optionally in combination with anadditional biologically active ingredient, or N-oxides or salts thereof,with one or more pharmaceutically or veterinarily acceptable carrierscomprising excipients and auxiliaries selected with regard to theintended route of administration (e.g., oral or parenteraladministration such as injection) and in accordance with standardpractice. In addition, a suitable carrier is selected on the basis ofcompatibility with the one or more active ingredients in thecomposition, including such considerations as stability relative to pHand moisture content. Therefore of note are compounds of the inventionfor protecting an animal from an invertebrate parasitic pest comprisinga parasitically effective amount of a compound of the invention,optionally in combination with an additional biologically activeingredient and at least one carrier.

For parenteral administration including intravenous, intramuscular andsubcutaneous injection, the compounds of the invention can be formulatedin suspension, solution or emulsion in oily or aqueous vehicles, and maycontain adjuncts such as suspending, stabilizing and/or dispersingagents.

The compounds of the invention may also be formulated for bolusinjection or continuous infusion. Pharmaceutical compositions forinjection include aqueous solutions of water-soluble forms of activeingredients (e.g., a salt of an active compound), preferably inphysiologically compatible buffers containing other excipients orauxiliaries as are known in the art of pharmaceutical formulation.Additionally, suspensions of the active compounds may be prepared in alipophilic vehicle. Suitable lipophilic vehicles include fatty oils suchas sesame oil, synthetic fatty acid esters such as ethyl oleate andtriglycerides, or materials such as liposomes.

Aqueous injection suspensions may contain substances that increase theviscosity of the suspension, such as sodium carboxymethyl cellulose,sorbitol, or dextran. Formulations for injection may be presented inunit dosage form, e.g., in ampoules or in multi-dose containers.Alternatively, the active ingredient may be in powder form forconstitution with a suitable vehicle, e.g., sterile, pyrogen-free water,before use.

In addition to the formulations described supra, the compounds of theinvention may also be formulated as a depot preparation. Such longacting formulations may be administered by implantation (for example,subcutaneously or intramuscularly) or by intramuscular or subcutaneousinjection.

The compounds of the invention may be formulated for this route ofadministration with suitable polymeric or hydrophobic materials (forinstance, in an emulsion with a pharmacologically acceptable oil), withion exchange resins, or as a sparingly soluble derivative such as,without limitation, a sparingly soluble salt.

For administration by inhalation, the compounds of the invention can bedelivered in the form of an aerosol spray using a pressurized pack or anebulizer and a suitable propellant, e.g., without limitation,dichlorodifluoromethane, trichlorofluoromethane,dichlorotetrafluoroethane or carbon dioxide. In the case of apressurized aerosol, the dosage unit may be controlled by providing avalve to deliver a metered amount.

Capsules and cartridges of, for example, gelatin for use in an inhaleror insufflator may be formulated containing a powder mix of the compoundand a suitable powder base such as lactose or starch.

The compounds of the invention may have favourable pharmacokinetic andpharmacodynamic properties providing systemic availability from oraladministration and ingestion. Therefore after ingestion by the animal tobe protected, parasiticidally effective concentrations of a compound ofthe invention in the bloodstream may protect the treated animal fromblood-sucking pests such as fleas, ticks and lice. Therefore of note isa composition for protecting an animal from an invertebrate parasitepest in a form for oral administration (i.e. comprising, in addition toa parasiticidally effective amount of a compound of the invention, oneor more carriers selected from binders and fillers suitable for oraladministration and feed concentrate carriers).

For oral administration in the form of solutions (the most readilyavailable form for absorption), emulsions, suspensions, pastes, gels,capsules, tablets, boluses, powders, granules, rumen-retention andfeed/water/lick blocks, the compounds of the invention can be formulatedwith binders/fillers known in the art to be suitable for oraladministration compositions, such as sugars and sugar derivatives (e.g.,lactose, sucrose, mannitol, sorbitol), starch (e.g., maize starch, wheatstarch, rice starch, potato starch), cellulose and derivatives (e.g.,methylcellulose, carboxymethylcellulose, ethylhydroxycellulose), proteinderivatives (e.g., zein, gelatin), and synthetic polymers (e.g.,polyvinyl alcohol, polyvinylpyrrolidone). If desired, lubricants (e.g.,magnesium stearate), disintegrating agents (e.g., cross-linkedpolyvinylpyrrolidinone, agar, alginic acid) and dyes or pigments can beadded. Pastes and gels often also contain adhesives (e.g., acacia,alginic acid, bentonite, cellulose, xanthan gum, colloidal magnesiumaluminum silicate) to aid in keeping the composition in contact with theoral cavity and not being easily ejected.

In one embodiment a composition of the present invention is formulatedinto a chewable and/or edible product (e.g., a chewable treat or edibletablet). Such a product would ideally have a taste, texture and/or aromafavored by the animal to be protected so as to facilitate oraladministration of the compounds of the invention.

If the parasiticidal compositions are in the form of feed concentrates,the carrier is typically selected from high-performance feed, feedcereals or protein concentrates.

Such feed concentrate-containing compositions can, in addition to theparasiticidal active ingredients, comprise additives promoting animalhealth or growth, improving quality of meat from animals for slaughteror otherwise useful to animal husbandry.

These additives can include, for example, vitamins, antibiotics,chemotherapeutics, bacteriostats, fungistats, coccidiostats andhormones.

The compound of the invention may also be formulated in rectalcompositions such as suppositories or retention enemas, using, e.g.,conventional suppository bases such as cocoa butter or other glycerides.

The formulations for the method of this invention may include anantioxidant, such as BHT (butylated hydroxytoluene). The antioxidant isgenerally present in amounts of at 0.1-5 percent (wt/vol). Some of theformulations require a solubilizer, such as oleic acid, to dissolve theactive agent, particularly if spinosad is included. Common spreadingagents used in these pour-on formulations include isopropyl myristate,isopropyl palmitate, caprylic/capric acid esters of saturated C₁₂-C₁₈fatty alcohols, oleic acid, oleyl ester, ethyl oleate, triglycerides,silicone oils and dipropylene glycol methyl ether. The pour-onformulations for the method of this invention are prepared according toknown techniques. Where the pour-on is a solution, theparasiticide/insecticide is mixed with the carrier or vehicle, usingheat and stirring if required. Auxiliary or additional ingredients canbe added to the mixture of active agent and carrier, or they can bemixed with the active agent prior to the addition of the carrier.Pour-on formulations in the form of emulsions or suspensions aresimilarly prepared using known techniques.

Other delivery systems for relatively hydrophobic pharmaceuticalcompounds may be employed. Liposomes and emulsions are well-knownexamples of delivery vehicles or carriers for hydrophobic drugs. Inaddition, organic solvents such as dimethylsulfoxide may be used, ifneeded.

The rate of application required for effective parasitic invertebratepest control (e.g. “pesticidally effective amount”) will depend on suchfactors as the species of parasitic invertebrate pest to be controlled,the pest's life cycle, life stage, its size, location, time of year,host crop or animal, feeding behavior, mating behavior, ambientmoisture, temperature, and the like. One skilled in the art can easilydetermine the pesticidally effective amount necessary for the desiredlevel of parasitic invertebrate pest control.

In general for veterinary use, the compounds of the invention areadministered in a pesticidally effective amount to an animal,particularly a homeothermic animal, to be protected from parasiticinvertebrate pests.

A pesticidally effective amount is the amount of active ingredientneeded to achieve an observable effect diminishing the occurrence oractivity of the target parasitic invertebrate pest. One skilled in theart will appreciate that the pesticidally effective dose can vary forthe various compounds and compositions useful for the method of thepresent invention, the desired pesticidal effect and duration, thetarget parasitic invertebrate pest species, the animal to be protected,the mode of application and the like, and the amount needed to achieve aparticular result can be determined through simple experimentation.

For oral or parenteral administration to animals, a dose of thecompositions of the present invention administered at suitable intervalstypically ranges from about 0.01 mg/kg to about 100 mg/kg, andpreferably from about 0.01 mg/kg to about 30 mg/kg of animal bodyweight.

Suitable intervals for the administration of the compositions of thepresent invention to animals range from about daily to about yearly. Ofnote are administration intervals ranging from about weekly to aboutonce every 6 months. Of particular note are monthly administrationintervals (i.e. administering the compounds to the animal once everymonth).

The present invention also provides a method for controlling pests (suchas mosquitoes and other disease vectors; see alsohttp://www.who.int/malaria/vector_control/irs/en/). In one embodiment,the method for controlling pests comprises applying the compositions ofthe invention to the target pests, to their locus or to a surface orsubstrate by brushing, rolling, spraying, spreading or dipping. By wayof example, an IRS (indoor residual spraying) application of a surfacesuch as a wall, ceiling or floor surface is contemplated by the methodof the invention. In another embodiment, it is contemplated to applysuch compositions to a substrate such as non-woven or a fabric materialin the form of (or which can be used in the manufacture of) netting,clothing, bedding, curtains and tents.

In one embodiment, the method for controlling such pests comprisesapplying a pesticidally effective amount of the compositions of theinvention to the target pests, to their locus, or to a surface orsubstrate so as to provide effective residual pesticidal activity on thesurface or substrate. Such application may be made by brushing, rolling,spraying, spreading or dipping the pesticidal composition of theinvention. By way of example, an IRS application of a surface such as awall, ceiling or floor surface is contemplated by the method of theinvention so as to provide effective residual pesticidal activity on thesurface. In another embodiment, it is contemplated to apply suchcompositions for residual control of pests on a substrate such as afabric material in the form of (or which can be used in the manufactureof) netting, clothing, bedding, curtains and tents.

Substrates including non-woven, fabrics or netting to be treated may bemade of natural fibres such as cotton, raffia, jute, flax, sisal,hessian, or wool, or synthetic fibres such as polyamide, polyester,polypropylene, polyacrylonitrile or the like. The polyesters areparticularly suitable. The methods of textile treatment are know, e.g.from Handbuch Textilveredlung: Band 1: Ausrüstung, Band 2: Farbgebung,Band 3: Beschichtung, Band 4: Umwelttechnik; Verlag: DeutscherFachverlag; Auflage: 15., iiberarbeitete Ausgabe (17. Apr. 2006);ISBN-10: 3866410123; ISBN-13: 978-3866410121, see especially Band 1:Ausrüstung pages 27-198, more preferably on page 118; or WO2008151984 orWO2003034823 or U.S. Pat. No. 5,631,072 or WO200564072 or WO2006128870or EP1724392 or WO2005064072 or WO2005113886 or WO2007090739.

The term “plant” as used herein includes seedlings, bushes and trees.

The term “crops” or “plant” is to be understood as including also cropplants which have been so transformed by the use of recombinant DNAtechniques that they are capable of synthesising one or more selectivelyacting toxins, such as are known, for example, from toxin-producingbacteria, especially those of the genus Bacillus.

Toxins that can be expressed by such transgenic plants include, forexample, insecticidal proteins, from Bacillus cereus or Bacilluspopilliae; or insecticidal proteins from Bacillus thuringiensis, such asδ-endotoxins, e.g. Cry1Ab, Cry1Ac, Cry1F, Cry1Fa2, Cry2Ab, Cry3A,Cry3Bb1 or Cry9C, or vegetative insecticidal proteins (Vip), e.g. Vip1,Vip2, Vip3 or Vip3 A; or insecticidal proteins of bacteria colonisingnematodes, for example Photorhabdus spp., or Xenorhabdus spp., such asPhotorhabdus luminescens, Xenorhabdus nematophilus; toxins produced byanimals, such as scorpion toxins, arachnid toxins, wasp toxins and otherinsect-specific neurotoxins; toxins produced by fungi, such asStreptomycetes toxins, plant lectins, such as pea lectins, barleylectins or snowdrop lectins; agglutinins; proteinase inhibitors, such astrypsin inhibitors, serine protease inhibitors, patatin, cystatin,papain inhibitors; ribosome-inactivating proteins (RIP), such as ricin,maize-RIP, abrin, luffin, saporin or bryodin; steroid metabolismenzymes, such as 3-hydroxysteroidoxidase,ecdysteroid-UDP-glycosyl-transferase, cholesterol oxidases, ecdysoneinhibitors, HMG-COA-reductase, ion channel blockers, such as blockers ofsodium or calcium channels, juvenile hormone esterase, diuretic hormonereceptors, stilbene synthase, bibenzyl synthase, chitinases andglucanases.

In the context of the present invention there are to be understood byδ-endotoxins, for example Cry1Ab, Cry1Ac, Cry1F, Cry1Fa2, Cry2Ab, Cry3A, Cry3Bb1 or Cry9C, or vegetative insecticidal proteins (Vip), forexample Vip1, Vip2, Vip3 or Vip3 A, expressly also hybrid toxins,truncated toxins and modified toxins. Hybrid toxins are producedrecombinantly by a new combination of different domains of thoseproteins (see, for example, WO 02/15701). Truncated toxins, for examplea truncated Cry1Ab, are known. In the case of modified toxins, one ormore amino acids of the naturally occurring toxin are replaced. In suchamino acid replacements, preferably non-naturally present proteaserecognition sequences are inserted into the toxin, such as, for example,in the case of Cry3 A055, a cathepsin-G-recognition sequence is insertedinto a Cry3 A toxin (see WO 03/018810).

Examples of such toxins or transgenic plants capable of synthesisingsuch toxins are disclosed, for example, in EP-A-0 374 753, WO 93/07278,WO 95/34656, EP-A-0 427 529, EP-A-451 878 and WO 03/052073.

The processes for the preparation of such transgenic plants aregenerally known to the person skilled in the art and are described, forexample, in the publications mentioned above. CryI-type deoxyribonucleicacids and their preparation are known, for example, from WO 95/34656,EP-A-0 367 474, EP-A-0 401 979 and WO 90/13651.

The toxin contained in the transgenic plants imparts to the plantstolerance to harmful insects. Such insects can occur in any taxonomicgroup of insects, but are especially commonly found in the beetles(Coleoptera), two-winged insects (Diptera) and butterflies(Lepidoptera).

Transgenic plants containing one or more genes that code for aninsecticidal resistance and express one or more toxins are known andsome of them are commercially available. Examples of such plants are:YieldGard® (maize variety that expresses a Cry1Ab toxin); YieldGardRootworm® (maize variety that expresses a Cry3Bb1 toxin); YieldGardPlus® (maize variety that expresses a Cry1Ab and a Cry3Bb1 toxin);Starlink® (maize variety that expresses a Cry9C toxin); Herculex I®(maize variety that expresses a Cry1Fa2 toxin and the enzymephosphinothricine N-acetyltransferase (PAT) to achieve tolerance to theherbicide glufosinate ammonium); NuCOTN 33B® (cotton variety thatexpresses a Cry1Ac toxin); Bollgard I® (cotton variety that expresses aCry1Ac toxin); Bollgard II® (cotton variety that expresses a Cry1Ac anda Cry2Ab toxin); VipCot® (cotton variety that expresses a Vip3 A and aCry1Ab toxin); NewLeaf® (potato variety that expresses a Cry3 A toxin);NatureGard®, Agrisure® GT Advantage (GA21 glyphosate-tolerant trait),Agrisure® CB Advantage (Bt11 corn borer (CB) trait) and Protecta®.

Further Examples of Such Transgenic Crops are:

1. Bt11 Maize from Syngenta Seeds SAS, Chemin de l'Hobit 27, F-31 790St. Sauveur, France, registration number C/FR/96/05/10. Geneticallymodified Zea mays which has been rendered resistant to attack by theEuropean corn borer (Ostrinia nubilalis and Sesamia nonagrioides) bytransgenic expression of a truncated Cry1Ab toxin. Bt11 maize alsotransgenically expresses the enzyme PAT to achieve tolerance to theherbicide glufosinate ammonium.

2. Bt176 Maize from Syngenta Seeds SAS, Chemin de l'Hobit 27, F-31 790St. Sauveur, France, registration number C/FR/96/05/10. Geneticallymodified Zea mays which has been rendered resistant to attack by theEuropean corn borer (Ostrinia nubilalis and Sesamia nonagrioides) bytransgenic expression of a Cry1Ab toxin. Bt176 maize also transgenicallyexpresses the enzyme PAT to achieve tolerance to the herbicideglufosinate ammonium.

3. MIR604 Maize from Syngenta Seeds SAS, Chemin de l'Hobit 27, F-31 790St. Sauveur, France, registration number C/FR/96/05/10. Maize which hasbeen rendered insect-resistant by transgenic expression of a modifiedCry3 A toxin. This toxin is Cry3 A055 modified by insertion of acathepsin-G-protease recognition sequence. The preparation of suchtransgenic maize plants is described in WO 03/018810.

4. MON 863 Maize from Monsanto Europe S.A. 270-272 Avenue de Tervuren,B-1150 Brussels, Belgium, registration number C/DE/02/9. MON 863expresses a Cry3Bb1 toxin and has resistance to certain Coleopterainsects.

5. IPC 531 Cotton from Monsanto Europe S.A. 270-272 Avenue de Tervuren,B-1150 Brussels, Belgium, registration number C/ES/96/02.

6. 1507 Maize from Pioneer Overseas Corporation, Avenue Tedesco, 7B-1160 Brussels, Belgium, registration number C/NL/00/10. Geneticallymodified maize for the expression of the protein Cry1F for achievingresistance to certain Lepidoptera insects and of the PAT protein forachieving tolerance to the herbicide glufosinate ammonium.

7. NK603×MON 810 Maize from Monsanto Europe S.A. 270-272 Avenue deTervuren, B-1150 Brussels, Belgium, registration number C/GB/02/M3/03.Consists of conventionally bred hybrid maize varieties by crossing thegenetically modified varieties NK603 and MON 810. NK603×MON 810 Maizetransgenically expresses the protein CP4 EPSPS, obtained fromAgrobacterium spp. strain CP4, which imparts tolerance to the herbicideRoundup® (contains glyphosate), and also a Cry1Ab toxin obtained fromBacillus thuringiensis subsp. kurstaki which brings about tolerance tocertain Lepidoptera, include the European corn borer.

The activity of the compositions according to the invention can bebroadened considerably, and adapted to prevailing circumstances, byadding other insecticidally, acaricidally and/or fungicidally activeingredients. The mixtures of the compounds of formula I with otherinsecticidally, acaricidally and/or fungicidally active ingredients mayalso have further surprising advantages which can also be described, ina wider sense, as synergistic activity. For example, better tolerance byplants, reduced phytotoxicity, insects can be controlled in theirdifferent development stages or better behaviour during theirproduction, for example during grinding or mixing, during their storageor during their use.

Suitable additions to active ingredients here are, for example,representatives of the following classes of active ingredients:organophosphorus compounds, nitrophenol derivatives, thioureas, juvenilehormones, formamidines, benzophenone derivatives, ureas, pyrrolederivatives, carbamates, pyrethroids, chlorinated hydrocarbons,acylureas, pyridylmethyleneamino derivatives, macrolides, neonicotinoidsand Bacillus thuringiensis preparations.

The following mixtures of the compounds of formula I with activeingredients are preferred (the abbreviation “TX” means “one specificcompound selected from the Table 1 (compounds 1.1 to 1.112) or aspecific compound selected from the Table 2 (compounds 2.1 to 2.112) ora specific compound selected from Table A (compounds 1 to 5), of thepresent invention”):

an adjuvant selected from the group of substances consisting ofpetroleum oils (alternative name) (628)+TX,

an acaricide selected from the group of substances consisting of1,1-bis(4-chlorophenyl)-2-ethoxyethanol (IUPAC name) (910)+TX,2,4-dichlorophenyl benzenesulfonate (IUPAC/Chemical Abstracts name)(1059)+TX, 2-fluoro-N-methyl-N-1-naphthylacetamide (IUPAC name)(1295)+TX, 4-chlorophenyl phenyl sulfone (IUPAC name) (981)+TX,abamectin (1)+TX, acequinocyl (3)+TX, acetoprole [CCN]+TX, acrinathrin(9)+TX, aldicarb (16)+TX, aldoxycarb (863)+TX, alpha-cypermethrin(202)+TX, amidithion (870)+TX, amidoflumet [CCN]+TX, amidothioate(872)+TX, amiton (875)+TX, amiton hydrogen oxalate (875)+TX, amitraz(24)+TX, aramite (881)+TX, arsenous oxide (882)+TX, AVI 382 (compoundcode)+TX, AZ 60541 (compound code)+TX, azinphos-ethyl (44)+TX,azinphos-methyl (45)+TX, azobenzene (IUPAC name) (888)+TX, azocyclotin(46)+TX, azothoate (889)+TX, benomyl (62)+TX, benoxafos (alternativename) [CCN]+TX, benzoximate (71)+TX, benzyl benzoate (IUPAC name)[CCN]+TX, bifenazate (74)+TX, bifenthrin (76)+TX, binapacryl (907)+TX,brofenvalerate (alternative name)+TX, bromocyclen (918)+TX, bromophos(920)+TX, bromophos-ethyl (921)+TX, bromopropylate (94)+TX, buprofezin(99)+TX, butocarboxim (103)+TX, butoxycarboxim (104)+TX, butylpyridaben(alternative name)+TX, calcium polysulfide (IUPAC name) (111)+TX,camphechlor (941)+TX, carbanolate (943)+TX, carbaryl (115)+TX,carbofuran (118)+TX, carbophenothion (947)+TX, CGA 50′439 (developmentcode) (125)+TX, chinomethionat (126)+TX, chlorbenside (959)+TX,chlordimeform (964)+TX, chlordimeform hydrochloride (964)+TX,chlorfenapyr (130)+TX, chlorfenethol (968)+TX, chlorfenson (970)+TX,chlorfensulphide (971)+TX, chlorfenvinphos (131)+TX, chlorobenzilate(975)+TX, chloromebuform (977)+TX, chloromethiuron (978)+TX,chloropropylate (983)+TX, chlorpyrifos (145)+TX, chlorpyrifos-methyl(146)+TX, chlorthiophos (994)+TX, cinerin I (696)+TX, cinerin II(696)+TX, cinerins (696)+TX, clofentezine (158)+TX, closantel(alternative name) [CCN]+TX, coumaphos (174)+TX, crotamiton (alternativename) [CCN]+TX, crotoxyphos (1010)+TX, cufraneb (1013)+TX, cyanthoate(1020)+TX, cyflumetofen (CAS Reg. No.: 400882-07-7)+TX, cyhalothrin(196)+TX, cyhexatin (199)+TX, cypermethrin (201)+TX, DCPM (1032)+TX, DDT(219)+TX, demephion (1037)+TX, demephion-O (1037)+TX,demephion-S(1037)+TX, demeton (1038)+TX, demeton-methyl (224)+TX,demeton-O (1038)+TX, demeton-O-methyl (224)+TX, demeton-S(1038)+TX,demeton-S-methyl (224)+TX, demeton-S-methylsulphon (1039)+TX,diafenthiuron (226)+TX, dialifos (1042)+TX, diazinon (227)+TX,dichlofluanid (230)+TX, dichlorvos (236)+TX, dicliphos (alternativename)+TX, dicofol (242)+TX, dicrotophos (243)+TX, dienochlor (1071)+TX,dimefox (1081)+TX, dimethoate (262)+TX, dinactin (alternative name)(653)+TX, dinex (1089)+TX, dinex-diclexine (1089)+TX, dinobuton(269)+TX, dinocap (270)+TX, dinocap-4 [CCN]+TX, dinocap-6 [CCN]+TX,dinocton (1090)+TX, dinopenton (1092)+TX, dinosulfon (1097)+TX,dinoterbon (1098)+TX, dioxathion (1102)+TX, diphenyl sulfone (IUPACname) (1103)+TX, disulfiram (alternative name) [CCN]+TX, disulfoton(278)+TX, DNOC (282)+TX, dofenapyn (1113)+TX, doramectin (alternativename) [CCN]+TX, endosulfan (294)+TX, endothion (1121)+TX, EPN (297)+TX,eprinomectin (alternative name) [CCN]+TX, ethion (309)+TX,ethoate-methyl (1134)+TX, etoxazole (320)+TX, etrimfos (1142)+TX,fenazaflor (1147)+TX, fenazaquin (328)+TX, fenbutatin oxide (330)+TX,fenothiocarb (337)+TX, fenpropathrin (342)+TX, fenpyrad (alternativename)+TX, fenpyroximate (345)+TX, fenson (1157)+TX, fentrifanil(1161)+TX, fenvalerate (349)+TX, fipronil (354)+TX, fluacrypyrim(360)+TX, fluazuron (1166)+TX, flubenzimine (1167)+TX, flucycloxuron(366)+TX, flucythrinate (367)+TX, fluenetil (1169)+TX, flufenoxuron(370)+TX, flumethrin (372)+TX, fluorbenside (1174)+TX, fluvalinate(1184)+TX, FMC 1137 (development code) (1185)+TX, formetanate (405)+TX,formetanate hydrochloride (405)+TX, formothion (1192)+TX, formparanate(1193)+TX, gamma-HCH (430)+TX, glyodin (1205)+TX, halfenprox (424)+TX,heptenophos (432)+TX, hexadecyl cyclopropanecarboxylate (IUPAC/ChemicalAbstracts name) (1216)+TX, hexythiazox (441)+TX, iodomethane (IUPACname) (542)+TX, isocarbophos (alternative name) (473)+TX, isopropylO-(methoxyaminothiophosphoryl)salicylate (IUPAC name) (473)+TX,ivermectin (alternative name) [CCN]+TX, jasmolin I (696)+TX, jasmolin II(696)+TX, jodfenphos (1248)+TX, lindane (430)+TX, lufenuron (490)+TX,malathion (492)+TX, malonoben (1254)+TX, mecarbam (502)+TX, mephosfolan(1261)+TX, mesulfen (alternative name) [CCN]+TX, methacrifos (1266)+TX,methamidophos (527)+TX, methidathion (529)+TX, methiocarb (530)+TX,methomyl (531)+TX, methyl bromide (537)+TX, metolcarb (550)+TX,mevinphos (556)+TX, mexacarbate (1290)+TX, milbemectin (557)+TX,milbemycin oxime (alternative name) [CCN]+TX, mipafox (1293)+TX,monocrotophos (561)+TX, morphothion (1300)+TX, moxidectin (alternativename) [CCN]+TX, naled (567)+TX, NC-184 (compound code)+TX, NC-512(compound code)+TX, nifluridide (1309)+TX, nikkomycins (alternativename) [CCN]+TX, nitrilacarb (1313)+TX, nitrilacarb 1:1 zinc chloridecomplex (1313)+TX, NNI-0101 (compound code)+TX, NNI-0250 (compoundcode)+TX, omethoate (594)+TX, oxamyl (602)+TX, oxydeprofos (1324)+TX,oxydisulfoton (1325)+TX, pp′-DDT (219)+TX, parathion (615)+TX,permethrin (626)+TX, petroleum oils (alternative name) (628)+TX,phenkapton (1330)+TX, phenthoate (631)+TX, phorate (636)+TX, phosalone(637)+TX, phosfolan (1338)+TX, phosmet (638)+TX, phosphamidon (639)+TX,phoxim (642)+TX, pirimiphos-methyl (652)+TX, polychloroterpenes(traditional name) (1347)+TX, polynactins (alternative name) (653)+TX,proclonol (1350)+TX, profenofos (662)+TX, promacyl (1354)+TX, propargite(671)+TX, propetamphos (673)+TX, propoxur (678)+TX, prothidathion(1360)+TX, prothoate (1362)+TX, pyrethrin I (696)+TX, pyrethrin II(696)+TX, pyrethrins (696)+TX, pyridaben (699)+TX, pyridaphenthion(701)+TX, pyrimidifen (706)+TX, pyrimitate (1370)+TX, quinalphos(711)+TX, quintiofos (1381)+TX, R-1492 (development code) (1382)+TX,RA-17 (development code) (1383)+TX, rotenone (722)+TX, schradan(1389)+TX, sebufos (alternative name)+TX, selamectin (alternative name)[CCN]+TX, SI-0009 (compound code)+TX, sophamide (1402)+TX, spirodiclofen(738)+TX, spiromesifen (739)+TX, SSI-121 (development code) (1404)+TX,sulfiram (alternative name) [CCN]+TX, sulfluramid (750)+TX, sulfotep(753)+TX, sulphur (754)+TX, SZI-121 (development code) (757)+TX,tau-fluvalinate (398)+TX, tebufenpyrad (763)+TX, TEPP (1417)+TX, terbam(alternative name)+TX, tetrachlorvinphos (777)+TX, tetradifon (786)+TX,tetranactin (alternative name) (653)+TX, tetrasul (1425)+TX, thiafenox(alternative name)+TX, thiocarboxime (1431)+TX, thiofanox (800)+TX,thiometon (801)+TX, thioquinox (1436)+TX, thuringiensin (alternativename) [CCN]+TX, triamiphos (1441)+TX, triarathene (1443)+TX, triazophos(820)+TX, triazuron (alternative name)+TX, trichlorfon (824)+TX,trifenofos (1455)+TX, trinactin (alternative name) (653)+TX, vamidothion(847)+TX, vaniliprole [CCN] and YI-5302 (compound code)+TX, an algicideselected from the group of substances consisting of bethoxazin [CCN]+TX,copper dioctanoate (IUPAC name) (170)+TX, copper sulfate (172)+TX,cybutryne [CCN]+TX, dichlone (1052)+TX, dichlorophen (232)+TX, endothal(295)+TX, fentin (347)+TX, hydrated lime [CCN]+TX, nabam (566)+TX,quinoclamine (714)+TX, quinonamid (1379)+TX, simazine (730)+TX,triphenyltin acetate (IUPAC name) (347) and triphenyltin hydroxide(IUPAC name) (347)+TX,an anthelmintic selected from the group of substances consisting ofabamectin (1)+TX, crufomate (1011)+TX, doramectin (alternative name)[CCN]+TX, emamectin (291)+TX, emamectin benzoate (291)+TX, eprinomectin(alternative name) [CCN]+TX, ivermectin (alternative name) [CCN]+TX,milbemycin oxime (alternative name) [CCN]+TX, moxidectin (alternativename) [CCN]+TX, piperazine [CCN]+TX, selamectin (alternative name)[CCN]+TX, spinosad (737) and thiophanate (1435)+TX,an avicide selected from the group of substances consisting ofchloralose (127)+TX, endrin (1122)+TX, fenthion (346)+TX,pyridin-4-amine (IUPAC name) (23) and strychnine (745)+TX, a bactericideselected from the group of substances consisting of1-hydroxy-1H-pyridine-2-thione (IUPAC name) (1222)+TX,4-(quinoxalin-2-ylamino)benzenesulfonamide (IUPAC name) (748)+TX,8-hydroxyquinoline sulfate (446)+TX, bronopol (97)+TX, copperdioctanoate (IUPAC name) (170)+TX, copper hydroxide (IUPAC name)(169)+TX, cresol [CCN]+TX, dichlorophen (232)+TX, dipyrithione(1105)+TX, dodicin (1112)+TX, fenaminosulf (1144)+TX, formaldehyde(404)+TX, hydrargaphen (alternative name) [CCN]+TX, kasugamycin(483)+TX, kasugamycin hydrochloride hydrate (483)+TX, nickelbis(dimethyldithiocarbamate) (IUPAC name) (1308)+TX, nitrapyrin(580)+TX, octhilinone (590)+TX, oxolinic acid (606)+TX, oxytetracycline(611)+TX, potassium hydroxyquinoline sulfate (446)+TX, probenazole(658)+TX, streptomycin (744)+TX, streptomycin sesquisulfate (744)+TX,tecloftalam (766)+TX, and thiomersal (alternative name) [CCN]+TX,a biological agent selected from the group of substances consisting ofAdoxophyes orana GV (alternative name) (12)+TX, Agrobacteriumradiobacter (alternative name) (13)+TX, Amblyseius spp. (alternativename) (19)+TX, Anagrapha falcifera NPV (alternative name) (28)+TX,Anagrus atomus (alternative name) (29)+TX, Aphelinus abdominalis(alternative name) (33)+TX, Aphidius colemani (alternative name)(34)+TX, Aphidoletes aphidimyza (alternative name) (35)+TX, Autographacalifornica NPV (alternative name) (38)+TX, Bacillus firmus (alternativename) (48)+TX, Bacillus sphaericus Neide (scientific name) (49)+TX,Bacillus thuringiensis Berliner (scientific name) (51)+TX, Bacillusthuringiensis subsp. aizawai (scientific name) (51)+TX, Bacillusthuringiensis subsp. israelensis (scientific name) (51)+TX, Bacillusthuringiensis subsp. japonensis (scientific name) (51)+TX, Bacillusthuringiensis subsp. kurstaki (scientific name) (51)+TX, Bacillusthuringiensis subsp. tenebrionis (scientific name) (51)+TX, Beauveriabassiana (alternative name) (53)+TX, Beauveria brongniartii (alternativename) (54)+TX, Chrysoperla carnea (alternative name) (151)+TX,Cryptolaemus montrouzieri (alternative name) (178)+TX, Cydia pomonellaGV (alternative name) (191)+TX, Dacnusa sibirica (alternative name)(212)+TX, Diglyphus isaea (alternative name) (254)+TX, Encarsia formosa(scientific name) (293)+TX, Eretmocerus eremicus (alternative name)(300)+TX, Helicoverpa zea NPV (alternative name) (431)+TX,Heterorhabditis bacteriophora and H. megidis (alternative name)(433)+TX, Hippodamia convergens (alternative name) (442)+TX, Leptomastixdactylopii (alternative name) (488)+TX, Macrolophus caliginosus(alternative name) (491)+TX, Mamestra brassicae NPV (alternative name)(494)+TX, Metaphycus helvolus (alternative name) (522)+TX, Metarhiziumanisopliae var. acridum (scientific name) (523)+TX, Metarhiziumanisopliae var. anisopliae (scientific name) (523)+TX, Neodiprionsertifer NPV and N. lecontei NPV (alternative name) (575)+TX, Orius spp.(alternative name) (596)+TX, Paecilomyces fumosoroseus (alternativename) (613)+TX, Phytoseiulus persimilis (alternative name) (644)+TX,Spodoptera exigua multicapsid nuclear polyhedrosis virus (scientificname) (741)+TX, Steinernema bibionis (alternative name) (742)+TX,Steinernema carpocapsae (alternative name) (742)+TX, Steinernema feltiae(alternative name) (742)+TX, Steinernema glaseri (alternative name)(742)+TX, Steinernema riobrave (alternative name) (742)+TX, Steinernemariobravis (alternative name) (742)+TX, Steinernema scapterisci(alternative name) (742)+TX, Steinernema spp. (alternative name)(742)+TX, Trichogramma spp. (alternative name) (826)+TX, Typhlodromusoccidentalis (alternative name) (844) and Verticillium lecanii(alternative name) (848)+TX,a soil sterilant selected from the group of substances consisting ofiodomethane (IUPAC name) (542) and methyl bromide (537)+TX,a chemosterilant selected from the group of substances consisting ofapholate [CCN]+TX, bisazir (alternative name) [CCN]+TX, busulfan(alternative name) [CCN]+TX, diflubenzuron (250)+TX, dimatif(alternative name) [CCN]+TX, hemel [CCN]+TX, hempa [CCN]+TX, metepa[CCN]+TX, methiotepa [CCN]+TX, methyl apholate [CCN]+TX, morzid[CCN]+TX, penfluron (alternative name) [CCN]+TX, tepa [CCN]+TX,thiohempa (alternative name) [CCN]+TX, thiotepa (alternative name)[CCN]+TX, tretamine (alternative name) [CCN] and uredepa (alternativename) [CCN]+TX,an insect pheromone selected from the group of substances consisting of(E)-dec-5-en-1-yl acetate with (E)-dec-5-en-1-ol (IUPAC name) (222)+TX,(E)-tridec-4-en-1-yl acetate (IUPAC name) (829)+TX,(E)-6-methylhept-2-en-4-ol (IUPAC name) (541)+TX,(E,Z)-tetradeca-4,10-dien-1-yl acetate (IUPAC name) (779)+TX,(Z)-dodec-7-en-1-yl acetate (IUPAC name) (285)+TX, (Z)-hexadec-11-enal(IUPAC name) (436)+TX, (Z)-hexadec-11-en-1-yl acetate (IUPAC name)(437)+TX, (Z)-hexadec-13-en-11-yn-1-yl acetate (IUPAC name) (438)+TX,(Z)-icos-13-en-10-one (IUPAC name) (448)+TX, (Z)-tetradec-7-en-1-al(IUPAC name) (782)+TX, (Z)-tetradec-9-en-1-ol (IUPAC name) (783)+TX,(Z)-tetradec-9-en-1-yl acetate (IUPAC name) (784)+TX,(7E,9Z)-dodeca-7,9-dien-1-yl acetate (IUPAC name) (283)+TX,(9Z,11E)-tetradeca-9,11-dien-1-yl acetate (IUPAC name) (780)+TX,(9Z,12E)-tetradeca-9,12-dien-1-yl acetate (IUPAC name) (781)+TX,14-methyloctadec-1-ene (IUPAC name) (545)+TX, 4-methylnonan-5-ol with4-methylnonan-5-one (IUPAC name) (544)+TX, alpha-multistriatin(alternative name) [CCN]+TX, brevicomin (alternative name) [CCN]+TX,codlelure (alternative name) [CCN]+TX, codlemone (alternative name)(167)+TX, cuelure (alternative name) (179)+TX, disparlure (277)+TX,dodec-8-en-1-yl acetate (IUPAC name) (286)+TX, dodec-9-en-1-yl acetate(IUPAC name) (287)+TX, dodeca-8+TX, 10-dien-1-yl acetate (IUPAC name)(284)+TX, dominicalure (alternative name) [CCN]+TX, ethyl4-methyloctanoate (IUPAC name) (317)+TX, eugenol (alternative name)[CCN]+TX, frontalin (alternative name) [CCN]+TX, gossyplure (alternativename) (420)+TX, grandlure (421)+TX, grandlure I (alternative name)(421)+TX, grandlure II (alternative name) (421)+TX, grandlure III(alternative name) (421)+TX, grandlure IV (alternative name) (421)+TX,hexalure [CCN]+TX, ipsdienol (alternative name) [CCN]+TX, ipsenol(alternative name) [CCN]+TX, japonilure (alternative name) (481)+TX,lineatin (alternative name) [CCN]+TX, litlure (alternative name)[CCN]+TX, looplure (alternative name) [CCN]+TX, medlure [CCN]+TX,megatomoic acid (alternative name) [CCN]+TX, methyl eugenol (alternativename) (540)+TX, muscalure (563)+TX, octadeca-2,13-dien-1-yl acetate(IUPAC name) (588)+TX, octadeca-3,13-dien-1-yl acetate (IUPAC name)(589)+TX, orfralure (alternative name) [CCN]+TX, oryctalure (alternativename) (317)+TX, ostramone (alternative name) [CCN]+TX, siglure [CCN]+TX,sordidin (alternative name) (736)+TX, sulcatol (alternative name)[CCN]+TX, tetradec-11-en-1-yl acetate (IUPAC name) (785)+TX, trimedlure(839)+TX, trimedlure A (alternative name) (839)+TX, trimedlure B₁(alternative name) (839)+TX, trimedlure B₂ (alternative name) (839)+TX,trimedlure C (alternative name) (839) and trunc-call (alternative name)[CCN]+TX,an insect repellent selected from the group of substances consisting of2-(octylthio)ethanol (IUPAC name) (591)+TX, butopyronoxyl (933)+TX,butoxy(polypropylene glycol) (936)+TX, dibutyl adipate (IUPAC name)(1046)+TX, dibutyl phthalate (1047)+TX, dibutyl succinate (IUPAC name)(1048)+TX, diethyltoluamide [CCN]+TX, dimethyl carbate [CCN]+TX,dimethyl phthalate [CCN]+TX, ethyl hexanediol (1137)+TX, hexamide[CCN]+TX, methoquin-butyl (1276)+TX, methylneodecanamide [CCN]+TX,oxamate [CCN] and picaridin [CCN]+TX, an insecticide selected from thegroup of substances consisting of 1-dichloro-1-nitroethane(IUPAC/Chemical Abstracts name) (1058)+TX,1,1-dichloro-2,2-bis(4-ethylphenyl)ethane (IUPAC name) (1056), +TX,1,2-dichloropropane (IUPAC/Chemical Abstracts name) (1062)+TX,1,2-dichloropropane with 1,3-dichloropropene (IUPAC name) (1063)+TX,1-bromo-2-chloroethane (IUPAC/Chemical Abstracts name) (916)+TX,2,2,2-trichloro-1-(3,4-dichlorophenyl)ethyl acetate (IUPAC name)(1451)+TX, 2,2-dichlorovinyl 2-ethylsulphinylethyl methyl phosphate(IUPAC name) (1066)+TX, 2-(1,3-dithiolan-2-yl)phenyl dimethylcarbamate(IUPAC/Chemical Abstracts name) (1109)+TX, 2-(2-butoxyethoxy)ethylthiocyanate (IUPAC/Chemical Abstracts name) (935)+TX,2-(4,5-dimethyl-1,3-dioxolan-2-yl)phenyl methylcarbamate (IUPAC/ChemicalAbstracts name) (1084)+TX, 2-(4-chloro-3,5-xylyloxy)ethanol (IUPAC name)(986)+TX, 2-chlorovinyl diethyl phosphate (IUPAC name) (984)+TX,2-imidazolidone (IUPAC name) (1225)+TX, 2-isovalerylindan-1,3-dione(IUPAC name) (1246)+TX, 2-methyl(prop-2-ynyl)aminophenyl methylcarbamate(IUPAC name) (1284)+TX, 2-thiocyanatoethyl laurate (IUPAC name)(1433)+TX, 3-bromo-1-chloroprop-1-ene (IUPAC name) (917)+TX,3-methyl-1-phenylpyrazol-5-yl dimethylcarbamate (IUPAC name) (1283)+TX,4-methyl(prop-2-ynyl)amino-3,5-xylyl methylcarbamate (IUPAC name)(1285)+TX, 5,5-dimethyl-3-oxocyclohex-1-enyl dimethylcarbamate (IUPACname) (1085)+TX, abamectin (1)+TX, acephate (2)+TX, acetamiprid (4)+TX,acethion (alternative name) [CCN]+TX, acetoprole [CCN]+TX, acrinathrin(9)+TX, acrylonitrile (IUPAC name) (861)+TX, alanycarb (15)+TX, aldicarb(16)+TX, aldoxycarb (863)+TX, aldrin (864)+TX, allethrin (17)+TX,allosamidin (alternative name) [CCN]+TX, allyxycarb (866)+TX,alpha-cypermethrin (202)+TX, alpha-ecdysone (alternative name) [CCN]+TX,aluminium phosphide (640)+TX, amidithion (870)+TX, amidothioate(872)+TX, aminocarb (873)+TX, amiton (875)+TX, amiton hydrogen oxalate(875)+TX, amitraz (24)+TX, anabasine (877)+TX, athidathion (883)+TX, AVI382 (compound code)+TX, AZ 60541 (compound code)+TX, azadirachtin(alternative name) (41)+TX, azamethiphos (42)+TX, azinphos-ethyl(44)+TX, azinphos-methyl (45)+TX, azothoate (889)+TX, Bacillusthuringiensis delta endotoxins (alternative name) (52)+TX, bariumhexafluorosilicate (alternative name) [CCN]+TX, barium polysulfide(IUPAC/Chemical Abstracts name) (892)+TX, barthrin [CCN]+TX, Bayer22/190 (development code) (893)+TX, Bayer 22408 (development code)(894)+TX, bendiocarb (58)+TX, benfuracarb (60)+TX, bensultap (66)+TX,beta-cyfluthrin (194)+TX, beta-cypermethrin (203)+TX, bifenthrin(76)+TX, bioallethrin (78)+TX, bioallethrin S-cyclopentenyl isomer(alternative name) (79)+TX, bioethanomethrin [CCN]+TX, biopermethrin(908)+TX, bioresmethrin (80)+TX, bis(2-chloroethyl) ether (IUPAC name)(909)+TX, bistrifluron (83)+TX, borax (86)+TX, brofenvalerate(alternative name)+TX, bromfenvinfos (914)+TX, bromocyclen (918)+TX,bromo-DDT (alternative name) [CCN]+TX, bromophos (920)+TX,bromophos-ethyl (921)+TX, bufencarb (924)+TX, buprofezin (99)+TX,butacarb (926)+TX, butathiofos (927)+TX, butocarboxim (103)+TX, butonate(932)+TX, butoxycarboxim (104)+TX, butylpyridaben (alternative name)+TX,cadusafos (109)+TX, calcium arsenate [CCN]+TX, calcium cyanide (444)+TX,calcium polysulfide (IUPAC name) (111)+TX, camphechlor (941)+TX,carbanolate (943)+TX, carbaryl (115)+TX, carbofuran (118)+TX, carbondisulfide (IUPAC/Chemical Abstracts name) (945)+TX, carbon tetrachloride(IUPAC name) (946)+TX, carbophenothion (947)+TX, carbosulfan (119)+TX,cartap (123)+TX, cartap hydrochloride (123)+TX, cevadine (alternativename) (725)+TX, chlorbicyclen (960)+TX, chlordane (128)+TX, chlordecone(963)+TX, chlordimeform (964)+TX, chlordimeform hydrochloride (964)+TX,chlorethoxyfos (129)+TX, chlorfenapyr (130)+TX, chlorfenvinphos(131)+TX, chlorfluazuron (132)+TX, chlormephos (136)+TX, chloroform[CCN]+TX, chloropicrin (141)+TX, chlorphoxim (989)+TX, chlorprazophos(990)+TX, chlorpyrifos (145)+TX, chlorpyrifos-methyl (146)+TX,chlorthiophos (994)+TX, chromafenozide (150)+TX, cinerin I (696)+TX,cinerin II (696)+TX, cinerins (696)+TX, cis-resmethrin (alternativename)+TX, cismethrin (80)+TX, clocythrin (alternative name)+TX,cloethocarb (999)+TX, closantel (alternative name) [CCN]+TX,clothianidin (165)+TX, copper acetoarsenite [CCN]+TX, copper arsenate[CCN]+TX, copper oleate [CCN]+TX, coumaphos (174)+TX, coumithoate(1006)+TX, crotamiton (alternative name) [CCN]+TX, crotoxyphos(1010)+TX, crufomate (1011)+TX, cryolite (alternative name) (177)+TX, CS708 (development code) (1012)+TX, cyanofenphos (1019)+TX, cyanophos(184)+TX, cyanthoate (1020)+TX, cyclethrin [CCN]+TX, cycloprothrin(188)+TX, cyfluthrin (193)+TX, cyhalothrin (196)+TX, cypermethrin(201)+TX, cyphenothrin (206)+TX, cyromazine (209)+TX, cythioate(alternative name) [CCN]+TX, d-limonene (alternative name) [CCN]+TX,d-tetramethrin (alternative name) (788)+TX, DAEP (1031)+TX, dazomet(216)+TX, DDT (219)+TX, decarbofuran (1034)+TX, deltamethrin (223)+TX,demephion (1037)+TX, demephion-O (1037)+TX, demephion-S (1037)+TX,demeton (1038)+TX, demeton-methyl (224)+TX, demeton-O (1038)+TX,demeton-O-methyl (224)+TX, demeton-S(1038)+TX, demeton-S-methyl(224)+TX, demeton-S-methylsulphon (1039)+TX, diafenthiuron (226)+TX,dialifos (1042)+TX, diamidafos (1044)+TX, diazinon (227)+TX, dicapthon(1050)+TX, dichlofenthion (1051)+TX, dichlorvos (236)+TX, dicliphos(alternative name)+TX, dicresyl (alternative name) [CCN]+TX, dicrotophos(243)+TX, dicyclanil (244)+TX, dieldrin (1070)+TX, diethyl5-methylpyrazol-3-yl phosphate (IUPAC name) (1076)+TX, diflubenzuron(250)+TX, dilor (alternative name) [CCN]+TX, dimefluthrin [CCN]+TX,dimefox (1081)+TX, dimetan (1085)+TX, dimethoate (262)+TX, dimethrin(1083)+TX, dimethylvinphos (265)+TX, dimetilan (1086)+TX, dinex(1089)+TX, dinex-diclexine (1089)+TX, dinoprop (1093)+TX, dinosam(1094)+TX, dinoseb (1095)+TX, dinotefuran (271)+TX, diofenolan(1099)+TX, dioxabenzofos (1100)+TX, dioxacarb (1101)+TX, dioxathion(1102)+TX, disulfoton (278)+TX, dithicrofos (1108)+TX, DNOC (282)+TX,doramectin (alternative name) [CCN]+TX, DSP (1115)+TX, ecdysterone(alternative name) [CCN]+TX, EI 1642 (development code) (1118)+TX,emamectin (291)+TX, emamectin benzoate (291)+TX, EMPC (1120)+TX,empenthrin (292)+TX, endosulfan (294)+TX, endothion (1121)+TX, endrin(1122)+TX, EPBP (1123)+TX, EPN (297)+TX, epofenonane (1124)+TX,eprinomectin (alternative name) [CCN]+TX, esfenvalerate (302)+TX,etaphos (alternative name) [CCN]+TX, ethiofencarb (308)+TX, ethion(309)+TX, ethiprole (310)+TX, ethoate-methyl (1134)+TX, ethoprophos(312)+TX, ethyl formate (IUPAC name) [CCN]+TX, ethyl-DDD (alternativename) (1056)+TX, ethylene dibromide (316)+TX, ethylene dichloride(chemical name) (1136)+TX, ethylene oxide [CCN]+TX, etofenprox (319)+TX,etrimfos (1142)+TX, EXD (1143)+TX, famphur (323)+TX, fenamiphos(326)+TX, fenazaflor (1147)+TX, fenchlorphos (1148)+TX, fenethacarb(1149)+TX, fenfluthrin (1150)+TX, fenitrothion (335)+TX, fenobucarb(336)+TX, fenoxacrim (1153)+TX, fenoxycarb (340)+TX, fenpirithrin(1155)+TX, fenpropathrin (342)+TX, fenpyrad (alternative name)+TX,fensulfothion (1158)+TX, fenthion (346)+TX, fenthion-ethyl [CCN]+TX,fenvalerate (349)+TX, fipronil (354)+TX, flonicamid (358)+TX,flubendiamide (CAS. Reg. No.: 272451-65-7)+TX, flucofuron (1168)+TX,flucycloxuron (366)+TX, flucythrinate (367)+TX, fluenetil (1169)+TX,flufenerim [CCN]+TX, flufenoxuron (370)+TX, flufenprox (1171)+TX,flumethrin (372)+TX, fluvalinate (1184)+TX, FMC 1137 (development code)(1185)+TX, fonofos (1191)+TX, formetanate (405)+TX, formetanatehydrochloride (405)+TX, formothion (1192)+TX, formparanate (1193)+TX,fosmethilan (1194)+TX, fospirate (1195)+TX, fosthiazate (408)+TX,fosthietan (1196)+TX, furathiocarb (412)+TX, furethrin (1200)+TX,gamma-cyhalothrin (197)+TX, gamma-HCH (430)+TX, guazatine (422)+TX,guazatine acetates (422)+TX, GY-81 (development code) (423)+TX,halfenprox (424)+TX, halofenozide (425)+TX, HCH (430)+TX, HEOD(1070)+TX, heptachlor (1211)+TX, heptenophos (432)+TX, heterophos[CCN]+TX, hexaflumuron (439)+TX, HHDN (864)+TX, hydramethylnon (443)+TX,hydrogen cyanide (444)+TX, hydroprene (445)+TX, hyquincarb (1223)+TX,imidacloprid (458)+TX, imiprothrin (460)+TX, indoxacarb (465)+TX,iodomethane (IUPAC name) (542)+TX, IPSP (1229)+TX, isazofos (1231)+TX,isobenzan (1232)+TX, isocarbophos (alternative name) (473)+TX, isodrin(1235)+TX, isofenphos (1236)+TX, isolane (1237)+TX, isoprocarb (472)+TX,isopropyl O-(methoxyaminothiophosphoryl)salicylate (IUPAC name)(473)+TX, isoprothiolane (474)+TX, isothioate (1244)+TX, isoxathion(480)+TX, ivermectin (alternative name) [CCN]+TX, jasmolin I (696)+TX,jasmolin II (696)+TX, jodfenphos (1248)+TX, juvenile hormone I(alternative name) [CCN]+TX, juvenile hormone II (alternative name)[CCN]+TX, juvenile hormone III (alternative name) [CCN]+TX, kelevan(1249)+TX, kinoprene (484)+TX, lambda-cyhalothrin (198)+TX, leadarsenate [CCN]+TX, lepimectin (CCN)+TX, leptophos (1250)+TX, lindane(430)+TX, lirimfos (1251)+TX, lufenuron (490)+TX, lythidathion(1253)+TX, m-cumenyl methylcarbamate (IUPAC name) (1014)+TX, magnesiumphosphide (IUPAC name) (640)+TX, malathion (492)+TX, malonoben(1254)+TX, mazidox (1255)+TX, mecarbam (502)+TX, mecarphon (1258)+TX,menazon (1260)+TX, mephosfolan (1261)+TX, mercurous chloride (513)+TX,mesulfenfos (1263)+TX, metaflumizone (CCN)+TX, metam (519)+TX,metam-potassium (alternative name) (519)+TX, metam-sodium (519)+TX,methacrifos (1266)+TX, methamidophos (527)+TX, methanesulphonyl fluoride(IUPAC/Chemical Abstracts name) (1268)+TX, methidathion (529)+TX,methiocarb (530)+TX, methocrotophos (1273)+TX, methomyl (531)+TX,methoprene (532)+TX, methoquin-butyl (1276)+TX, methothrin (alternativename) (533)+TX, methoxychlor (534)+TX, methoxyfenozide (535)+TX, methylbromide (537)+TX, methyl isothiocyanate (543)+TX, methylchloroform(alternative name) [CCN]+TX, methylene chloride [CCN]+TX, metofluthrin[CCN]+TX, metolcarb (550)+TX, metoxadiazone (1288)+TX, mevinphos(556)+TX, mexacarbate (1290)+TX, milbemectin (557)+TX, milbemycin oxime(alternative name) [CCN]+TX, mipafox (1293)+TX, mirex (1294)+TX,monocrotophos (561)+TX, morphothion (1300)+TX, moxidectin (alternativename) [CCN]+TX, naftalofos (alternative name) [CCN]+TX, naled (567)+TX,naphthalene (IUPAC/Chemical Abstracts name) (1303)+TX, NC-170(development code) (1306)+TX, NC-184 (compound code)+TX, nicotine(578)+TX, nicotine sulfate (578)+TX, nifluridide (1309)+TX, nitenpyram(579)+TX, nithiazine (1311)+TX, nitrilacarb (1313)+TX, nitrilacarb 1:1zinc chloride complex (1313)+TX, NNI-0101 (compound code)+TX, NNI-0250(compound code)+TX, nornicotine (traditional name) (1319)+TX, novaluron(585)+TX, noviflumuron (586)+TX, O-5-dichloro-4-iodophenyl O-ethylethylphosphonothioate (IUPAC name) (1057)+TX, O,O-diethylO-4-methyl-2-oxo-2H-chromen-7-yl phosphorothioate (IUPAC name)(1074)+TX, O,O-diethyl O-6-methyl-2-propylpyrimidin-4-ylphosphorothioate (IUPAC name) (1075)+TX, O,O,O′,O′-tetrapropyldithiopyrophosphate (IUPAC name) (1424)+TX, oleic acid (IUPAC name)(593)+TX, omethoate (594)+TX, oxamyl (602)+TX, oxydemeton-methyl(609)+TX, oxydeprofos (1324)+TX, oxydisulfoton (1325)+TX, pp′-DDT(219)+TX, para-dichlorobenzene [CCN]+TX, parathion (615)+TX,parathion-methyl (616)+TX, penfluron (alternative name) [CCN]+TX,pentachlorophenol (623)+TX, pentachlorophenyl laurate (IUPAC name)(623)+TX, permethrin (626)+TX, petroleum oils (alternative name)(628)+TX, PH 60-38 (development code) (1328)+TX, phenkapton (1330)+TX,phenothrin (630)+TX, phenthoate (631)+TX, phorate (636)+TX, phosalone(637)+TX, phosfolan (1338)+TX, phosmet (638)+TX, phosnichlor (1339)+TX,phosphamidon (639)+TX, phosphine (IUPAC name) (640)+TX, phoxim (642)+TX,phoxim-methyl (1340)+TX, pirimetaphos (1344)+TX, pirimicarb (651)+TX,pirimiphos-ethyl (1345)+TX, pirimiphos-methyl (652)+TX,polychlorodicyclopentadiene isomers (IUPAC name) (1346)+TX,polychloroterpenes (traditional name) (1347)+TX, potassium arsenite[CCN]+TX, potassium thiocyanate [CCN]+TX, prallethrin (655)+TX,precocene I (alternative name) [CCN]+TX, precocene II (alternative name)[CCN]+TX, precocene III (alternative name) [CCN]+TX, primidophos(1349)+TX, profenofos (662)+TX, profluthrin [CCN]+TX, promacyl(1354)+TX, promecarb (1355)+TX, propaphos (1356)+TX, propetamphos(673)+TX, propoxur (678)+TX, prothidathion (1360)+TX, prothiofos(686)+TX, prothoate (1362)+TX, protrifenbute [CCN]+TX, pymetrozine(688)+TX, pyraclofos (689)+TX, pyrazophos (693)+TX, pyresmethrin(1367)+TX, pyrethrin I (696)+TX, pyrethrin II (696)+TX, pyrethrins(696)+TX, pyridaben (699)+TX, pyridalyl (700)+TX, pyridaphenthion(701)+TX, pyrimidifen (706)+TX, pyrimitate (1370)+TX, pyriproxyfen(708)+TX, quassia (alternative name) [CCN]+TX, quinalphos (711)+TX,quinalphos-methyl (1376)+TX, quinothion (1380)+TX, quintiofos (1381)+TX,R-1492 (development code) (1382)+TX, rafoxanide (alternative name)[CCN]+TX, resmethrin (719)+TX, rotenone (722)+TX, RU 15525 (developmentcode) (723)+TX, RU 25475 (development code) (1386)+TX, ryania(alternative name) (1387)+TX, ryanodine (traditional name) (1387)+TX,sabadilla (alternative name) (725)+TX, schradan (1389)+TX, sebufos(alternative name)+TX, selamectin (alternative name) [CCN]+TX, SI-0009(compound code)+TX, SI-0205 (compound code)+TX, SI-0404 (compoundcode)+TX, SI-0405 (compound code)+TX, silafluofen (728)+TX, SN 72129(development code) (1397)+TX, sodium arsenite [CCN]+TX, sodium cyanide(444)+TX, sodium fluoride (IUPAC/Chemical Abstracts name) (1399)+TX,sodium hexafluorosilicate (1400)+TX, sodium pentachlorophenoxide(623)+TX, sodium selenate (IUPAC name) (1401)+TX, sodium thiocyanate[CCN]+TX, sophamide (1402)+TX, spinosad (737)+TX, spiromesifen (739)+TX,spirotetrmat (CCN)+TX, sulcofuron (746)+TX, sulcofuron-sodium (746)+TX,sulfluramid (750)+TX, sulfotep (753)+TX, sulphuryl fluoride (756)+TX,sulprofos (1408)+TX, tar oils (alternative name) (758)+TX,tau-fluvalinate (398)+TX, tazimcarb (1412)+TX, TDE (1414)+TX,tebufenozide (762)+TX, tebufenpyrad (763)+TX, tebupirimfos (764)+TX,teflubenzuron (768)+TX, tefluthrin (769)+TX, temephos (770)+TX, TEPP(1417)+TX, terallethrin (1418)+TX, terbam (alternative name)+TX,terbufos (773)+TX, tetrachloroethane [CCN]+TX, tetrachlorvinphos(777)+TX, tetramethrin (787)+TX, theta-cypermethrin (204)+TX,thiacloprid (791)+TX, thiafenox (alternative name)+TX, thiamethoxam(792)+TX, thicrofos (1428)+TX, thiocarboxime (1431)+TX, thiocyclam(798)+TX, thiocyclam hydrogen oxalate (798)+TX, thiodicarb (799)+TX,thiofanox (800)+TX, thiometon (801)+TX, thionazin (1434)+TX, thiosultap(803)+TX, thiosultap-sodium (803)+TX, thuringiensin (alternative name)[CCN]+TX, tolfenpyrad (809)+TX, tralomethrin (812)+TX, transfluthrin(813)+TX, transpermethrin (1440)+TX, triamiphos (1441)+TX, triazamate(818)+TX, triazophos (820)+TX, triazuron (alternative name)+TX,trichlorfon (824)+TX, trichlormetaphos-3 (alternative name) [CCN]+TX,trichloronat (1452)+TX, trifenofos (1455)+TX, triflumuron (835)+TX,trimethacarb (840)+TX, triprene (1459)+TX, vamidothion (847)+TX,vaniliprole [CCN]+TX, veratridine (alternative name) (725)+TX, veratrine(alternative name) (725)+TX, XMC (853)+TX, xylylcarb (854)+TX, YI-5302(compound code)+TX, zeta-cypermethrin (205)+TX, zetamethrin (alternativename)+TX, zinc phosphide (640)+TX, zolaprofos (1469) and ZXI 8901(development code) (858)+TX, cyantraniliprole [736994-63-19]+TX,chlorantraniliprole [500008-45-7]+TX, cyenopyrafen [560121-52-0]+TX,cyflumetofen [400882-07-7]+TX, pyrifluquinazon [337458-27-2]+TX,spinetoram [187166-40-1+187166-15-0]+TX, spirotetramat [203313-25-1]+TX,sulfoxaflor [946578-00-3]+TX, flufiprole [704886-18-0]+TX, meperfluthrin[915288-13-0]+TX, tetramethylfluthrin [84937-88-2]+TX,a molluscicide selected from the group of substances consisting ofbis(tributyltin) oxide (IUPAC name) (913)+TX, bromoacetamide [CCN]+TX,calcium arsenate [CCN]+TX, cloethocarb (999)+TX, copper acetoarsenite[CCN]+TX, copper sulfate (172)+TX, fentin (347)+TX, ferric phosphate(IUPAC name) (352)+TX, metaldehyde (518)+TX, methiocarb (530)+TX,niclosamide (576)+TX, niclosamide-olamine (576)+TX, pentachlorophenol(623)+TX, sodium pentachlorophenoxide (623)+TX, tazimcarb (1412)+TX,thiodicarb (799)+TX, tributyltin oxide (913)+TX, trifenmorph (1454)+TX,trimethacarb (840)+TX, triphenyltin acetate (IUPAC name) (347) andtriphenyltin hydroxide (IUPAC name) (347)+TX, pyriprole[394730-71-3]+TX,a nematicide selected from the group of substances consisting ofAKD-3088 (compound code)+TX, 1,2-dibromo-3-chloropropane (IUPAC/ChemicalAbstracts name) (1045)+TX, 1,2-dichloropropane (IUPAC/Chemical Abstractsname) (1062)+TX, 1,2-dichloropropane with 1,3-dichloropropene (IUPACname) (1063)+TX, 1,3-dichloropropene (233)+TX,3,4-dichlorotetrahydrothiophene 1,1-dioxide (IUPAC/Chemical Abstractsname) (1065)+TX, 3-(4-chlorophenyl)-5-methylrhodanine (IUPAC name)(980)+TX, 5-methyl-6-thioxo-1,3,5-thiadiazinan-3-ylacetic acid (IUPACname) (1286)+TX, 6-isopentenylaminopurine (alternative name) (210)+TX,abamectin (1)+TX, acetoprole [CCN]+TX, alanycarb (15)+TX, aldicarb(16)+TX, aldoxycarb (863)+TX, AZ 60541 (compound code)+TX, benclothiaz[CCN]+TX, benomyl (62)+TX, butylpyridaben (alternative name)+TX,cadusafos (109)+TX, carbofuran (118)+TX, carbon disulfide (945)+TX,carbosulfan (119)+TX, chloropicrin (141)+TX, chlorpyrifos (145)+TX,cloethocarb (999)+TX, cytokinins (alternative name) (210)+TX, dazomet(216)+TX, DBCP (1045)+TX, DCIP (218)+TX, diamidafos (1044)+TX,dichlofenthion (1051)+TX, dicliphos (alternative name)+TX, dimethoate(262)+TX, doramectin (alternative name) [CCN]+TX, emamectin (291)+TX,emamectin benzoate (291)+TX, eprinomectin (alternative name) [CCN]+TX,ethoprophos (312)+TX, ethylene dibromide (316)+TX, fenamiphos (326)+TX,fenpyrad (alternative name)+TX, fensulfothion (1158)+TX, fosthiazate(408)+TX, fosthietan (1196)+TX, furfural (alternative name) [CCN]+TX,GY-81 (development code) (423)+TX, heterophos [CCN]+TX, iodomethane(IUPAC name) (542)+TX, isamidofos (1230)+TX, isazofos (1231)+TX,ivermectin (alternative name) [CCN]+TX, kinetin (alternative name)(210)+TX, mecarphon (1258)+TX, metam (519)+TX, metam-potassium(alternative name) (519)+TX, metam-sodium (519)+TX, methyl bromide(537)+TX, methyl isothiocyanate (543)+TX, milbemycin oxime (alternativename) [CCN]+TX, moxidectin (alternative name) [CCN]+TX, Myrotheciumverrucaria composition (alternative name) (565)+TX, NC-184 (compoundcode)+TX, oxamyl (602)+TX, phorate (636)+TX, phosphamidon (639)+TX,phosphocarb [CCN]+TX, sebufos (alternative name)+TX, selamectin(alternative name) [CCN]+TX, spinosad (737)+TX, terbam (alternativename)+TX, terbufos (773)+TX, tetrachlorothiophene (IUPAC/ChemicalAbstracts name) (1422)+TX, thiafenox (alternative name)+TX, thionazin(1434)+TX, triazophos (820)+TX, triazuron (alternative name)+TX,xylenols [CCN]+TX, YI-5302 (compound code) and zeatin (alternative name)(210)+TX, fluensulfone [318290-98-1]+TX, a nitrification inhibitorselected from the group of substances consisting of potassiumethylxanthate [CCN] and nitrapyrin (580)+TX,a plant activator selected from the group of substances consisting ofacibenzolar (6)+TX, acibenzolar-S-methyl (6)+TX, probenazole (658) andReynoutria sachalinensis extract (alternative name) (720)+TX,a rodenticide selected from the group of substances consisting of2-isovalerylindan-1,3-dione (IUPAC name) (1246)+TX,4-(quinoxalin-2-ylamino)benzenesulfonamide (IUPAC name) (748)+TX,alpha-chlorohydrin [CCN]+TX, aluminium phosphide (640)+TX, antu(880)+TX, arsenous oxide (882)+TX, barium carbonate (891)+TX,bisthiosemi (912)+TX, brodifacoum (89)+TX, bromadiolone (91)+TX,bromethalin (92)+TX, calcium cyanide (444)+TX, chloralose (127)+TX,chlorophacinone (140)+TX, cholecalciferol (alternative name) (850)+TX,coumachlor (1004)+TX, coumafuryl (1005)+TX, coumatetralyl (175)+TX,crimidine (1009)+TX, difenacoum (246)+TX, difethialone (249)+TX,diphacinone (273)+TX, ergocalciferol (301)+TX, flocoumafen (357)+TX,fluoroacetamide (379)+TX, flupropadine (1183)+TX, flupropadinehydrochloride (1183)+TX, gamma-HCH (430)+TX, HCH (430)+TX, hydrogencyanide (444)+TX, iodomethane (IUPAC name) (542)+TX, lindane (430)+TX,magnesium phosphide (IUPAC name) (640)+TX, methyl bromide (537)+TX,norbormide (1318)+TX, phosacetim (1336)+TX, phosphine (IUPAC name)(640)+TX, phosphorus [CCN]+TX, pindone (1341)+TX, potassium arsenite[CCN]+TX, pyrinuron (1371)+TX, scilliroside (1390)+TX, sodium arsenite[CCN]+TX, sodium cyanide (444)+TX, sodium fluoroacetate (735)+TX,strychnine (745)+TX, thallium sulfate [CCN]+TX, warfarin (851) and zincphosphide (640)+TX,a synergist selected from the group of substances consisting of2-(2-butoxyethoxy)ethyl piperonylate (IUPAC name) (934)+TX,5-(1,3-benzodioxol-5-yl)-3-hexylcyclohex-2-enone (IUPAC name) (903)+TX,farnesol with nerolidol (alternative name) (324)+TX, MB-599 (developmentcode) (498)+TX, MGK 264 (development code) (296)+TX, piperonyl butoxide(649)+TX, piprotal (1343)+TX, propyl isomer (1358)+TX, S421 (developmentcode) (724)+TX, sesamex (1393)+TX, sesasmolin (1394) and sulfoxide(1406)+TX,an animal repellent selected from the group of substances consisting ofanthraquinone (32)+TX, chloralose (127)+TX, copper naphthenate [CCN]+TX,copper oxychloride (171)+TX, diazinon (227)+TX, dicyclopentadiene(chemical name) (1069)+TX, guazatine (422)+TX, guazatine acetates(422)+TX, methiocarb (530)+TX, pyridin-4-amine (IUPAC name) (23)+TX,thiram (804)+TX, trimethacarb (840)+TX, zinc naphthenate [CCN] and ziram(856)+TX,a virucide selected from the group of substances consisting of imanin(alternative name) [CCN] and ribavirin (alternative name) [CCN]+TX,a wound protectant selected from the group of substances consisting ofmercuric oxide (512)+TX, octhilinone (590) and thiophanate-methyl(802)+TX,and biologically active compounds selected from the group consisting ofazaconazole (60207-31-0]+TX, bitertanol [70585-36-3]+TX, bromuconazole[116255-48-2]+TX, cyproconazole [94361-06-5]+TX, difenoconazole[119446-68-3]+TX, diniconazole [83657-24-3]+TX, epoxiconazole[106325-08-0]+TX, fenbuconazole [114369-43-6]+TX, fluquinconazole[136426-54-5]+TX, flusilazole [85509-19-9]+TX, flutriafol[76674-21-0]+TX, hexaconazole [79983-71-4]+TX, imazalil [35554-44-0]+TX,imibenconazole [86598-92-7]+TX, ipconazole [125225-28-7]+TX, metconazole[125116-23-6]+TX, myclobutanil [88671-89-0]+TX, pefurazoate[101903-30-4]+TX, penconazole [66246-88-6]+TX, prothioconazole[178928-70-6]+TX, pyrifenox [88283-41-4]+TX, prochloraz [67747-09-5]+TX,propiconazole [60207-90-1]+TX, simeconazole [149508-90-7]+TX,tebuconazole [107534-96-3]+TX, tetraconazole [112281-77-3]+TX,triadimefon [43121-43-3]+TX, triadimenol [55219-65-3]+TX, triflumizole[99387-89-0]+TX, triticonazole [131983-72-7]+TX, ancymidol[12771-68-5]+TX, fenarimol [60168-88-9]+TX, nuarimol [63284-71-9]+TX,bupirimate [41483-43-6]+TX, dimethirimol [5221-53-4]+TX, ethirimol[23947-60-6]+TX, dodemorph [1593-77-7]+TX, fenpropidine [67306-00-7]+TX,fenpropimorph [67564-91-4]+TX, spiroxamine [118134-30-8]+TX, tridemorph[81412-43-3]+TX, cyprodinil [121552-61-2]+TX, mepanipyrim[110235-47-7]+TX, pyrimethanil [53112-28-0]+TX, fenpiclonil[74738-17-3]+TX, fludioxonil [131341-86-1]+TX, benalaxyl[71626-11-4]+TX, furalaxyl [57646-30-7]+TX, metalaxyl [57837-19-1]+TX,R-metalaxyl [70630-17-0]+TX, ofurace [58810-48-3]+TX, oxadixyl[77732-09-3]+TX, benomyl [17804-35-2]+TX, carbendazim [10605-21-7]+TX,debacarb [62732-91-6]+TX, fuberidazole [3878-19-1]+TX, thiabendazole[148-79-8]+TX, chlozolinate [84332-86-5]+TX, dichlozoline[24201-58-9]+TX, iprodione [36734-19-7]+TX, myclozoline [54864-61-8]+TX,procymidone [32809-16-8]+TX, vinclozoline [50471-44-8]+TX, boscalid[188425-85-6]+TX, carboxin [5234-68-4]+TX, fenfuram [24691-80-3]+TX,flutolanil [66332-96-5]+TX, mepronil [55814-41-0]+TX, oxycarboxin[5259-88-1]+TX, penthiopyrad [183675-82-3]+TX, thifluzamide[130000-40-7]+TX, guazatine [108173-90-6]+TX, dodine [2439-10-3][112-65-2](free base)+TX, iminoctadine [13516-27-3]+TX, azoxystrobin[131860-33-8]+TX, dimoxystrobin [149961-52-4]+TX, enestroburin {Proc.BCPC, Int. Congr., Glasgow, 2003, 1, 93}+TX, fluoxastrobin[361377-29-9]+TX, kresoxim-methyl [143390-89-0]+TX, metominostrobin[133408-50-1]+TX, trifloxystrobin [141517-21-7]+TX, orysastrobin[248593-16-0]+TX, picoxystrobin [117428-22-5]+TX, pyraclostrobin[175013-18-0]+TX, ferbam [14484-64-1]+TX, mancozeb [8018-01-7]+TX, maneb[12427-38-2]+TX, metiram [9006-42-2]+TX, propineb [12071-83-9]+TX,thiram [137-26-8]+TX, zineb [12122-67-7]+TX, ziram [137-30-4]+TX,captafol [2425-06-1]+TX, captan [133-06-2]+TX, dichlofluanid[1085-98-9]+TX, fluoroimide [41205-21-4]+TX, folpet [133-07-3]+TX,tolylfluanid [731-27-1]+TX, bordeaux mixture [8011-63-0]+TX,copperhydroxid [20427-59-2]+TX, copperoxychlorid [1332-40-7]+TX,coppersulfat [7758-98-7]+TX, copperoxid [1317-39-1]+TX, mancopper[53988-93-5]+TX, oxine-copper [10380-28-6]+TX, dinocap [131-72-6]+TX,nitrothal-isopropyl [10552-74-6]+TX, edifenphos [17109-49-8]+TX,iprobenphos [26087-47-8]+TX, isoprothiolane [50512-35-1]+TX, phosdiphen[36519-00-3]+TX, pyrazophos [13457-18-6]+TX, tolclofos-methyl[57018-04-9]+TX, acibenzolar-S-methyl [135158-54-2]+TX, anilazine[101-05-3]+TX, benthiavalicarb [413615-35-7]+TX, blasticidin-S[2079-00-7]+TX, chinomethionat [2439-01-2]+TX, chloroneb [2675-77-6]+TX,chlorothalonil [1897-45-6]+TX, cyflufenamid [180409-60-3]+TX, cymoxanil[57966-95-7]+TX, dichlone [117-80-6]+TX, diclocymet [139920-32-4]+TX,diclomezine [62865-36-5]+TX, dicloran [99-30-9]+TX, diethofencarb[87130-20-9]+TX, dimethomorph [110488-70-5]+TX, SYP-L190 (Flumorph)[211867-47-9]+TX, dithianon [3347-22-6]+TX, ethaboxam [162650-77-3]+TX,etridiazole [2593-15-9]+TX, famoxadone [131807-57-3]+TX, fenamidone[161326-34-7]+TX, fenoxanil [115852-48-7]+TX, fentin [668-34-8]+TX,ferimzone [89269-64-7]+TX, fluazinam [79622-59-6]+TX, fluopicolide[239110-15-7]+TX, flusulfamide [106917-52-6]+TX, fenhexamid[126833-17-8]+TX, fosetyl-aluminium [39148-24-8]+TX, hymexazol[10004-44-1]+TX, iprovalicarb [140923-17-7]+TX, IKF-916 (Cyazofamid)[120116-88-3]+TX, kasugamycin [6980-18-3]+TX, methasulfocarb[66952-49-6]+TX, metrafenone [220899-03-6]+TX, pencycuron[66063-05-6]+TX, phthalide [27355-22-2]+TX, polyoxins [11113-80-7]+TX,probenazole [27605-76-1]+TX, propamocarb [25606-41-1]+TX, proquinazid[189278-12-4]+TX, pyroquilon [57369-32-1]+TX, quinoxyfen[124495-18-7]+TX, quintozene [82-68-8]+TX, sulphur [7704-34-9]+TX,tiadinil [223580-51-6]+TX, triazoxide [72459-58-6]+TX, tricyclazole[41814-78-2]+TX, triforine [26644-46-2]+TX, validamycin [37248-47-8]+TX,zoxamide (RH7281) [156052-68-5]+TX, mandipropamid [374726-62-2]+TX,isopyrazam [881685-58-1]+TX, sedaxane [874967-67-6]+TX,3-difluoromethyl-1-methyl-1H-pyrazole-4-carboxylic acid(9-dichloromethylene-1,2,3,4-tetrahydro-1,4-methano-naphthalen-5-yl)-amide(dislosed in WO 2007/048556)+TX,3-difluoromethyl-1-methyl-1H-pyrazole-4-carboxylic acid[2-(2,4-dichlorophenyl)-2-methoxy-1-methyl-ethyl]-amide (disclosed in WO2008/148570)+TX,1-[4-[4-[(5S)5-(2,6-difluorophenyl)-4,5-dihydro-1,2-oxazol-3-yl]-1,3-thiazol-2-yl]piperidin-1-yl]-2-[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]ethanone+TX,1-[4-[4-[5-(2,6-difluorophenyl)-4,5-dihydro-1,2-oxazol-3-yl]-1,3-thiazol-2-yl]piperidin-1-yl]-2-[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]ethanone[1003318-67-9], both disclosed in WO 2010/123791, WO 2008/013925, WO2008/013622 and WO 2011/051243 page 20)+TX,3-difluoromethyl-1-methyl-1H-pyrazole-4-carboxylic acid(3′,4′,5′-trifluoro-biphenyl-2-yl)-amide (disclosed in WO 2006/087343)+TX, and 1-methyl-2-(2,4,5-trichloro-thiophen-3-yl)-ethyl]+TX.

The references in brackets behind the active ingredients, e.g.[3878-19-1] refer to the Chemical Abstracts Registry number. The abovedescribed mixing partners are known. Where the active ingredients areincluded in “The Pesticide Manual” [The Pesticide Manual—A WorldCompendium; Thirteenth Edition; Editor: C. D. S. TomLin; The BritishCrop Protection Council], they are described therein under the entrynumber given in round brackets hereinabove for the particular compound;for example, the compound “abamectin” is described under entry number(1). Where “[CCN]” is added hereinabove to the particular compound, thecompound in question is included in the “Compendium of Pesticide CommonNames”, which is accessible on the internet [A. Wood; Compendium ofPesticide Common Names, Copyright © 1995-2004]; for example, thecompound “acetoprole” is described under the internet addresshttp://www.alanwood.net/pesticides/acetoprole.html.

Most of the active ingredients described above are referred tohereinabove by a so-called “common name”, the relevant “ISO common name”or another “common name” being used in individual cases.

If the designation is not a “common name”, the nature of the designationused instead is given in round brackets for the particular compound; inthat case, the IUPAC name, the IUPAC/Chemical Abstracts name, a“chemical name”, a “traditional name”, a “compound name” or a“development code” is used or, if neither one of those designations nora “common name” is used, an “alternative name” is employed. “CAS Reg.No” means the Chemical Abstracts Registry Number.

The active ingredient mixture of the compounds of formula I selectedfrom table P with active ingredients described above comprises onespecific compound selected from the Table 1 (compounds 1.1 to 1.112) ora specific compound selected from the Table 2 (compounds 2.1 to 2.112)or a specific compound selected from Table A (compounds 1 to 5), and anactive ingredient as described above preferably in a mixing ratio offrom 100:1 to 1:6000, especially from 50:1 to 1:50, more especially in aratio of from 20:1 to 1:20, even more especially from 10:1 to 1:10, veryespecially from 5:1 and 1:5, special preference being given to a ratioof from 2:1 to 1:2, and a ratio of from 4:1 to 2:1 being likewisepreferred, above all in a ratio of 1:1, or 5:1, or 5:2, or 5:3, or 5:4,or 4:1, or 4:2, or 4:3, or 3:1, or 3:2, or 2:1, or 1:5, or 2:5, or 3:5,or 4:5, or 1:4, or 2:4, or 3:4, or 1:3, or 2:3, or 1:2, or 1:600, or1:300, or 1:150, or 1:35, or 2:35, or 4:35, or 1:75, or 2:75, or 4:75,or 1:6000, or 1:3000, or 1:1500, or 1:350, or 2:350, or 4:350, or 1:750,or 2:750, or 4:750. Those mixing ratios are understood to include, onthe one hand, ratios by weight and also, on the other hand, molarratios.

The mixtures as described above can be used in a method for controllingpests, which comprises applying a composition comprising a mixture asdescribed above to the pests or their environment, with the exception ofa method for treatment of the human or animal body by surgery or therapyand diagnostic methods practised on the human or animal body.

The mixtures comprising a compound of formula I or one specific compoundselected from the Table 1 (compounds 1.1 to 1.112) or a specificcompound selected from the Table 2 (compounds 2.1 to 2.112) or aspecific compound selected from Table A (compounds 1 to 5),) and one ormore active ingredients as described above can be applied, for example,in a single “ready-mix” form, in a combined spray mixture composed fromseparate formulations of the single active ingredient components, suchas a “tank-mix”, and in a combined use of the single active ingredientswhen applied in a sequential manner, i.e. one after the other with areasonably short period, such as a few hours or days. The order ofapplying the compounds of formula I or one specific compound selectedfrom the Table 1 (compounds 1.1 to 1.112) or a specific compoundselected from the Table 2 (compounds 2.1 to 2.112) or a specificcompound selected from Table A (compounds 1 to 5), and the activeingredients as described above is not essential for working the presentinvention.

The compositions can also comprise further solid or liquid auxiliaries,such as stabilizers, for example unepoxidized or epoxidized vegetableoils (for example epoxidized coconut oil, rapeseed oil or soya oil),antifoams, for example silicone oil, preservatives, viscosityregulators, binders and/or tackifiers, fertilizers or other activeingredients for achieving specific effects, for example bactericides,fungicides, nematocides, plant activators, molluscicides or herbicides.

The compositions according to the invention are prepared in a mannerknown per se, in the absence of auxiliaries for example by grinding,screening and/or compressing a solid active ingredient and in thepresence of at least one auxiliary for example by intimately mixingand/or grinding the active ingredient with the auxiliary (auxiliaries).These processes for the preparation of the compositions and the use ofthe compounds I for the preparation of these compositions are also asubject of the invention.

The application methods for the compositions, that is the methods ofcontrolling pests of the abovementioned type, such as spraying,atomizing, dusting, brushing on, dressing, scattering or pouring—whichare to be selected to suit the intended aims of the prevailingcircumstances—and the use of the compositions for controlling pests ofthe abovementioned type are other subjects of the invention. Typicalrates of concentration are between 0.1 and 1000 ppm, preferably between0.1 and 500 ppm, of active ingredient. The rate of application perhectare is generally 1 to 2000 g of active ingredient per hectare, inparticular 10 to 1000 g/ha, preferably 10 to 600 g/ha.

A preferred method of application in the field of crop protection isapplication to the foliage of the plants (foliar application), it beingpossible to select frequency and rate of application to match the dangerof infestation with the pest in question. Alternatively, the activeingredient can reach the plants via the root system (systemic action),by drenching the locus of the plants with a liquid composition or byincorporating the active ingredient in solid form into the locus of theplants, for example into the soil, for example in the form of granules(soil application). In the case of paddy rice crops, such granules canbe metered into the flooded paddy-field.

The compositions according to the invention are also suitable for theprotection of plant propagation material, for example seeds, such asfruit, tubers or kernels, or nursery plants, against pests of theabovementioned type. The propagation material can be treated with thecompositions prior to planting, for example seed can be treated prior tosowing. Alternatively, the compositions can be applied to seed kernels(coating), either by soaking the kernels in a liquid composition or byapplying a layer of a solid composition. It is also possible to applythe compositions when the propagation material is planted to the site ofapplication, for example into the seed furrow during drilling. Thesetreatment methods for plant propagation material and the plantpropagation material thus treated are further subjects of the invention.

The compounds of formula (I) according to the invention can also be usedin combination with safeners. Preferably, in these mixtures, thecompound of the formula (I) or one specific compound selected from theTable 1 (compounds 1.1 to 1.112) or a specific compound selected fromthe Table 2 (compounds 2.1 to 2.112) or a specific compound selectedfrom Table A (compounds 1 to 5). The following mixtures with safeners,especially, come into consideration:

compound of formula (I)+cloquintocet-mexyl, compound of formula(I)+cloquintocet acid and salts thereof, compound of formula(I)+fenchlorazole-ethyl, compound of formula (I)+fenchlorazole acid andsalts thereof, compound of formula (I)+mefenpyr-diethyl, compound offormula (I)+mefenpyr diacid, compound of formula (I)+isoxadifen-ethyl,compound of formula (I)+isoxadifen acid, compound of formula(I)+furilazole, compound of formula (I)+furilazole R isomer, compound offormula (I)+benoxacor, compound of formula (I)+dichlormid, compound offormula (I)+AD-67, compound of formula (I)+oxabetrinil, compound offormula (I)+cyometrinil, compound of formula (I)+cyometrinil Z-isomer,compound of formula (I)+fenclorim, compound of formula(I)+cyprosulfamide, compound of formula (I)+naphthalic anhydride,compound of formula (I)+flurazole, compound of formula(I)+N-(2-methoxybenzoyl)-4-[(methylaminocarbonyl)amino]benzenesulfonamide,compound of formula (I)+CL 304,415, compound of formula (I)+dicyclonon,compound of formula (I)+fluxofenim, compound of formula (I)+DKA-24,compound of formula (I)+R-29148 and compound of formula (I)+PPG-1292. Asafening effect can also be observed for the mixtures compound of theformula (I)+dymron, compound of the formula (I)+MCPA, compound of theformula (I)+mecoprop and compound of the formula (I)+mecoprop-P.

The mixing partners of the TX may also be in the form of esters orsalts, as mentioned e.g. in The Pesticide Manual, 12th Edition (BCPC),2000.

In the above different lists of active ingredients to be mixed with aTX, the compound of the formula I is preferably one specific compoundselected from the Table 1 (compounds 1.1 to 1.112) or a specificcompound selected from the Table 2 (compounds 2.1 to 2.112) or aspecific compound selected from Table A (compounds 1 to 5).

In the above-mentioned mixtures of compounds of formula I, in particularone specific compound selected from the Table 1 (compounds 1.1 to 1.112)or a specific compound selected from the Table 2 (compounds 2.1 to2.112) or a specific compound selected from Table A (compounds 1 to 5),with other insecticides, fungicides, herbicides, safeners, adjuvants andthe like, the mixing ratios can vary over a large range and are,preferably

100:1 to 1:6000, especially 50:1 to 1:50, more especially 20:1 to 1:20,even more especially 10:1 to 1:10. Those mixing ratios are understood toinclude, on the one hand, ratios by weight and also, on the other hand,molar ratios.

The mixtures can advantageously be used in the above-mentionedformulations (in which case “active ingredient” relates to therespective mixture of TX with the mixing partner).

Some mixtures may comprise active ingredients which have significantlydifferent physical, chemical or biological properties such that they donot easily lend themselves to the same conventional formulation type. Inthese circumstances other formulation types may be prepared. Forexample, where one active ingredient is a water insoluble solid and theother a water insoluble liquid, it may nevertheless be possible todisperse each active ingredient in the same continuous aqueous phase bydispersing the solid active ingredient as a suspension (using apreparation analogous to that of an SC) but dispersing the liquid activeingredient as an emulsion (using a preparation analogous to that of anEW). The resultant composition is a suspoemulsion (SE) formulation.

The mixtures comprising a TX one specific compound selected from theTable 1 (compounds 1.1 to 1.112) or a specific compound selected fromthe Table 2 (compounds 2.1 to 2.112) or a specific compound selectedfrom Table A (compounds 1 to 5), and one or more active ingredients asdescribed above can be applied, for example, in a single “ready-mix”form, in a combined spray mixture composed from separate formulations ofthe single active ingredient components, such as a “tank-mix”, and in acombined use of the single active ingredients when applied in asequential manner, i.e. one after the other with a reasonably shortperiod, such as a few hours or days. The order of applying the compoundsof formula I or one specific compound selected from the Table 1(compounds 1.1 to 1.112) or a specific compound selected from the Table2 (compounds 2.1 to 2.112) or a specific compound selected from Table A(compounds 1 to 5), and the active ingredients as described above is notessential for working the present invention.

The compounds of formula (I) may be mixed with soil, peat or otherrooting media for the protection of plants against seed-borne,soil-borne or foliar fungal diseases.

Examples of suitable synergists for use in the compositions includepiperonyl butoxide, sesamex, safroxan and dodecyl imidazole.

Suitable herbicides and plant-growth regulators for inclusion in thecompositions will depend upon the intended target and the effectrequired.

An example of a rice selective herbicide which may be included ispropanil. An example of a plant growth regulator for use in cotton isPIX™

Some mixtures may comprise active ingredients which have significantlydifferent physical, chemical or biological properties such that they donot easily lend themselves to the same conventional formulation type. Inthese circumstances other formulation types may be prepared. Forexample, where one active ingredient is a water insoluble solid and theother a water insoluble liquid, it may nevertheless be possible todisperse each active ingredient in the same continuous aqueous phase bydispersing the solid active ingredient as a suspension (using apreparation analogous to that of an SC) but dispersing the liquid activeingredient as an emulsion (using a preparation analogous to that of anEW). The resultant composition is a suspoemulsion (SE) formulation.

The following Examples illustrate, but do not limit, the invention.

PREPARATION EXAMPLES Examples

The following abbreviations were used throughout this section:s=singlet; bs=broad singlet; d=doublet; dd=double doublet; dt=doubletriplet; t=triplet, tt=triple triplet, q=quartet, sept=septet;m=multiplet; Me=methyl; Et=ethyl; Pr=propyl; Bu=butyl; M.p.=meltingpoint.

Example I 1.1:N-[2-bromo-6-chloro-4-(1,1,1,2,3,3,3-heptafluoro-prop-2-yl)phenyl]-2-fluoro-3-nitro-benzamide

To a suspension of 2-fluoro-3-nitrobenzoic acid (309 g, 1.67 mol) indichloroethane (2090 ml) was added N,N-dimethylformamide (1.3 ml, 16.7mmol) followed by slow addition of oxalyl chloride (150 ml, 1.69 mol) atambient temperature. The reaction mixture was stirred and heated at 50°C. until a solution was formed. The reaction mixture was allowed to coolto ambient temperature and then added to a solution of2-bromo-6-chloro-4-[1,1,1,2,3,3,3-heptafluoro-prop-2-yl]aniline(described in WO/10127926) (125 g, 334 mmol) in dichloroethane (477 ml)followed by addition of triethylamine (564 ml, 4.01 mol). The reactionmixture was stirred at reflux for 4 hours. The reaction was quenched byaddition of saturated aqueous sodium hydrogen carbonate (500 ml). Thelayers were separated and the organic layer was washed with water (500ml). The combined aqueous layers were extracted twice withdichloroethane (2×500 ml). The combined organic extracts were dried oversodium sulfate and concentrated. The crude residue was dissolved in THFand a 1N solution of sodium hydroxide (2 eq) was added. The mixture wasstirred at room temperature until the diacylated product disappeared.Then ethyl acetate (1 L) and saturated aqueous sodium hydrogen carbonate(1 L) were added. The layers were separated and the aqueous layer wasextracted with ethyl acetate (4×250 ml). The organic layer wasconcentrated, filtered through silica gel, and concentrated again. Theresidue (181 g) was used directly for the next step.

¹H NMR (CDCl₃, 400 MHz): 8.39 (m, 1H), 8.21 (m, 1H), 8.09 (d, 1H), 7.78(s, 1H), 7.67 (s, 1H), 7.43 (t, 1H).

Preparation Examples Examples

The following abbreviations were used throughout this section:s=singlet; bs=broad singlet; d=doublet; dd=double doublet; dt=doubletriplet; t=triplet, tt=triple triplet, q=quartet, sept=septet;m=multiplet; Me=methyl; Et=ethyl; Pr=propyl; Bu=butyl; M.p.=meltingpoint.

Example I 1.1:N-[2-bromo-6-chloro-4-(1,1,1,2,3,3,3-heptafluoro-prop-2-yl)phenyl]-2-fluoro-3-nitro-benzamide

To a suspension of 2-fluoro-3-nitrobenzoic acid (309 g, 1.67 mol) indichloroethane (2090 ml) was added N,N-dimethylformamide (1.3 ml, 16.7mmol) followed by slow addition of oxalyl chloride (150 ml, 1.69 mol) atambient temperature. The reaction mixture was stirred and heated at 50°C. until a solution was formed. The reaction mixture was allowed to coolto ambient temperature and then added to a solution of2-bromo-6-chloro-4-[1,1,1,2,3,3,3-heptafluoro-prop-2-yl]aniline(described in WO/10127926) (125 g, 334 mmol) in dichloroethane (477 ml)followed by addition of triethylamine (564 ml, 4.01 mol). The reactionmixture was stirred at reflux for 4 hours. The reaction was quenched byaddition of saturated aqueous sodium hydrogen carbonate (500 ml). Thelayers were separated and the organic layer was washed with water (500ml). The combined aqueous layers were extracted twice withdichloroethane (2×500 ml). The combined organic extracts were dried oversodium sulfate and concentrated. The crude residue was dissolved in THFand a 1N solution of sodium hydroxide (2 eq) was added. The mixture wasstirred at room temperature until the diacylated product disappeared.Then ethyl acetate (1 L) and saturated aqueous sodium hydrogen carbonate(1 L) were added. The layers were separated and the aqueous layer wasextracted with ethyl acetate (4×250 ml). The organic layer wasconcentrated, filtered through silica gel, and concentrated again. Theresidue (181 g) was used directly for the next step.

¹H NMR (CDCl₃, 400 MHz): 8.39 (m, 1H), 8.21 (m, 1H), 8.09 (d, 1H), 7.78(s, 1H), 7.67 (s, 1H), 7.43 (t, 1H).

Example I 2.1:3-Amino-N-[2-bromo-6-chloro-4-(1,2,2,2,3,3,3-heptafluoro-prop-2-yl)-phenyl]-2-fluoro-benzamide

N-[2-bromo-6-chloro-4-(1,2,2,2,3,3,3-heptafluoro-prop-2-yl)phenyl]-2-fluoro-3-nitro-benzamide(Example I 1.1) (2 g, 3.69 mmol) was dissolved in THF (16.6 ml). ThenNaOH (9.2 ml), tetrabutylammonium bromide (0.121 g, 0.369 mmol) andsodium dithionite (2.27 g, 11.1 mmol) were added. The mixture was heatedunder reflux for 1.5 hours and then cooled down to room temperature. Thereaction mixture was diluted with ethyl acetate, water was added and thephases were separated. The aqueous phase was extracted twice with ethylacetate. The combined organic phases were washed with 1N aqueous HCl andthen with a aqueous solution of sodium hydrogen carbonate, dried oversodium sulfate, filtered and concentrated. Flashchromatography (eluent:cyclohexane/ethyl acetate from 100:0 to 0:100) gave3-amino-N-[2-bromo-6-chloro-4-(1,2,2,2,3,3,3-heptafluoro-prop-2-yl)-phenyl]-2-fluoro-benzamide(1.13 g, 59.6% yield).

¹H NMR (400 MHz, CDCl₃): 8.25 (d, 1H), 7.85 (s, 1H), 7.74 (s, 1H) 7.52(td, 1H), 7.12 (t, 1H), 7.03 (td, 1H), 3.80 (bs, 2H) ppm.

Example I 3.1:N-[2-bromo-6-chloro-4-(1,1,1,2,3,3,3-heptafluoro-prop-2-yl)-phenyl]-3-ethylamino-2-fluoro-benzamide

3-amino-N-[2-bromo-6-chloro-4-(1,2,2,2,3,3,3-heptafluoro-prop-2-yl)-phenyl]-2-fluoro-benzamide(Example I 2.1) (0.585 g, 1.14 mmol) was dissolved in methanol (8.2 ml)and acetaldehyde (0.065 ml, 1.14 mmol) and acetic acid (0.07 ml, 1.26mmol) were added. Then cyanoborohydride (0.083 g, 1.26 mmol) was added.The reaction mixture was stirred for 1 hour at room temperature. Afterevaporation of the solvent ethyl acetate and an aqueous solution ofsodium hydroxide (0.1M) were added. The layers were separated and theaqueous layer was extracted twice with ethyl acetate. The combinedorganic layers were washed with water, dried over magnesium sulfate,filtered and concentrated. The residue was purified by flashchromatography (eluent: cyclohexane/ethyl acetate 100:0=>50:50) to giveN-[2-bromo-6-chloro-4-(1,1,1,2,3,3,3-heptafluoro-prop-2-yl)-phenyl]-3-ethylamino-2-fluoro-benzamide(0.418 g, 68%).

¹H NMR (400 MHz, CDCl₃): 8.23 (d, 1H), 7.85 (s, 1H), 7.72 (s, 1H), 7.40(td, 1H), 7.17 (t, 1H), 6.92 (td, 1H), 4.01 (bs, 1H), 3.28 (q, 2H), 1.36(t, 3H) ppm.

Example P 1.1:N′-[3-[[2-bromo-6-chloro-4-[1,1,1,2,3,3,3-heptafluoro-prop-2-yl]phenyl]carbamoyl]-2-fluoro-phenyl]-N-ethyl-pyridine-4-carboxamide(Compound No. 1 of Table A)

N-[2-bromo-6-chloro-4-(1,1,1,2,3,3,3-heptafluoro-prop-2-yl)-phenyl]-3-ethylamino-2-fluoro-benzamide(Example I 3.1) (418 mg, 0.775 mmol) was dissolved in tetrahydrofuran(4.3 ml). Pyridine (0.25 ml, 3.1 mmol) and isonicotinoyl chloridehydrochloride (290 mg, 1.55 mol) were added and the reaction mixture wasstirred at ambient temperature for 16 hours. The reaction mixture waspoured into aqueous sodium hydrogen carbonate. The aqueous phase wasextracted twice with ethyl acetate. The combined organic phases weredried over sodium sulfate, filtered and concentrated. The residue waspurified by column chromatography on silica gel (eluent: ethylacetate/cyclohexane 20/80=>0:100). The fractions containing the desiredproduct were combined and the solvents were evaporated to give purecompound No. 1 of Table A (500 mg, quantitative). M.p. 99-101° C.

¹H NMR (400 MHz, CDCl₃): 8.51 (bs, 2H), 7.90-8.15 (m, 2H), 7.86 (s, 1H),7.72 (s, 1H), 7.25-7.62 (m, 2H), 7.20 (bs, 2H), 3.60-4.18 (m, 2H),1.20-1.40 (m, 3H) ppm.

Example P1.2:N′-[3-[[2-bromo-6-chloro-4-[1,1,1,2,3,3,3-heptafluoro-prop-2-yl]phenyl]carbamoyl]-2-fluoro-phenyl]-N-ethyl-1-oxido-pyridin-1-ium-4-carboxamide(Compound No. 2 of Table A)

N′-[3-[[2-bromo-6-chloro-4-[1,1,1,2,3,3,3-heptafluoro-prop-2-yl]phenyl]carbamoyl]-2-fluoro-phenyl]-N-ethyl-pyridine-4-carboxamide(Example P 1.1; compound No. 1 of Table A) (0.320 g, 0.496 mmol) wasdissolved in dichloromethane (3 ml) 3-chloroperoxybenzoic acid (0.245 g,0.993 mmol) was added. After stirring for 1 h at room temperature themixture was diluted with water and an aqueous solution of sodiumhydrogen carbonate. The phases were separated and the aqueous phase wasextracted with dichloromethane. The combined organic phases were driedover magnesium sulfate, filtered and concentrated. The residue waspurified by column chromatography on silica gel (eluent: DCM/MeOH from100:0 to 85:15) to give pure compound No. 2 of Table A (304 mg, 93%yield). M.p. 115-117° C. ¹H NMR (400 MHz, CDCl₃): 8.00-8.18 (m, 4H),7.84 (s, 1H), 7.72 (s, 1H), 7.40-7.52 (m, 1H) 7.32-7.40 (m, 1H),7.19-7.30 (m, 2H), 3.87-4.15 (m, 2H), 1.28 (t, 3H) ppm.

LC-MS Methods: ZCQ12, ZCQ13 and OA STANDARD

ZQ Mass Spectrometer from Waters (Single Quadrupole Mass Spectrometer)

Instrument Parameter:

Ionization method: Electrospray

Polarity: positive and negative ions

Capillary: 3.00 kV

Cone: 30 V

Extractor: 2.00 V

Source Temperature: 150° C.,

Desolvation Temperature: 350 C

Cone Gas Flow: 50 L/Hr

Desolvation Gas Flow: 400 L/Hr

Mass range: 100 to 900 Da

Acquity UPLC from Waters:

Binary pump, heated column compartment and diode-array detector.

Solvent degasser, binary pump, heated column compartment and diode-arraydetector.

Column: Waters UPLC HSS T3, 1.8 μm, 30×2.1 mm,

Temp: 60° C.

DAD Wavelength range (nm): 210 to 500

Solvent Gradient:

-   -   A=H2O+5% MeOH+0.05% HCOOH    -   B=Acetonitril+0.05% HCOOH

Time A % B % Flow (ml/min) 0.00 90 10 0.85 1.20 0 100.0 0.85 1.50 0100.0 0.85LC-MS Method: ZDQ11ZQ Mass Spectrometer from Waters (Single Quadrupole Mass Spectrometer)Instrument Parameter:

Ionization method: Electrospray

Polarity: positive and negative ions

Capillary: 3.00 kV

Cone: 30 V

Extractor: 2.00 V

Source Temperature: 150° C.,

Desolvation Temperature: 350C

Cone Gas Flow: 50 L/Hr

Desolvation Gas Flow: 400 L/Hr

Mass range: 100 to 900 Da

Acquity UPLC from Waters:

Binary pump, heated column compartment and diode-array detector.

Solvent degasser, binary pump, heated column compartment and diode-arraydetector.

Column: Waters UPLC HSS T3, 1.8 μm, 30×2.1 mm,

Temp: 60° C.

DAD Wavelength range (nm): 210 to 500

Solvent Gradient:

-   -   A=H2O+5% MeOH+0.05% HCOOH    -   B=Acetonitril+0.05% HCOOH

Time A % B % Flow (ml/min) 0.00 90 10 0.85 2.70 0 100.0 0.85 3.00 0100.0 0.85

The compounds in tables A were prepared in the same or a similar way asdescribed above:

TABLE A RT [M + H] Entry STRUCTURE (min) (measured) Method MP° C. 1

1.89 644, 646, 648 ZDQ11  99-101 2

1.80 660, 662, 664 ZDQ11 115-117 3

1.05 630, 632, 634 ZCQ12  99-160 4

1.11 588 ZCQ12 190-193 5

1.03 604 ZCQ12 105-111 6

1.07 688, 690, 692 ZCQ13  97-100 7

1.07 676, 678 ZCQ13 186-188 8

1.05 674, 676, 678 OA_STANDARD 112-250 9

0.97 690, 692, 694 OA_STANDARD 146-262 10

1.03 586, 588, 590 OA_STANDARD  85-90 11

1.07 600, 602, 604 OA_STANDARD  91-94 12

1.04 566, 568 OA_STANDARD  99-100 13

1.10 594, 596 OA_STANDARD 14

1.07 580, 582 OA_STANDARD 15

1.12 650, 652 OA_STANDARD  97-100 16

1.05 666, 668 OA_STANDARD 110-114 17

1.01 692, 694 OA_STANDARD 103-106 18

1.08 632, 634 OA_STANDARD 183-184 19

1.07 612 OA_STANDARD 186-188

Biological Examples

These Examples illustrate the insecticidal and acaricidal properties ofthe compounds of formula (I). The tests were performed as follows:

Spodoptera littoralis (Egyptian Cotton Leafworm):

Cotton leaf discs were placed on agar in a 24-well microtiter plate andsprayed with test solutions at an application rate of 200 ppm. Afterdrying, the leaf discs were infested with 5 L1 larvae. The samples werechecked for mortality, feeding behavior, and growth regulation 3 daysafter treatment (DAT).

The following compound gave at least 80% control of Spodopteralittoralis: 1, 2, 3, 4, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18,19.

Heliothis virescens (Tobacco Budworm):

Eggs (0-24 h old) were placed in 24-well microtiter plate on artificialdiet and treated with test solutions at an application rate of 200 ppm(concentration in well 18 ppm) by pipetting. After an incubation periodof 4 days, samples were checked for egg mortality, larval mortality, andgrowth regulation.

The following compound gave at least 80% control of Heliothis virescens:1, 2, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17.

Plutella xylostella (Diamond Back Moth):

24-well microtiter plate (MTP) with artificial diet was treated withtest solutions at an application rate of 200 ppm (concentration in well18 ppm) by pipetting. After drying, the MTP's were infested with L2larvae (7-12 per well). After an incubation period of 6 days, sampleswere checked for larval mortality and growth regulation.

The following compound gave at least 80% control of Plutella xylostella:1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19.

Diabrotica balteata (Corn Root Worm):

A 24-well microtiter plate (MTP) with artificial diet was treated withtest solutions at an application rate of 200 ppm (concentration in well18 ppm) by pipetting. After drying, the MTP's were infested with L2larvae (6-10 per well). After an incubation period of 5 days, sampleswere checked for larval mortality and growth regulation.

The following compound gave at least 80% control of Diabrotica balteata:1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19.

Thrips tabaci (Onion Thrips):

Sunflower leaf discs were placed on agar in a 24-well microtiter plateand sprayed with test solutions at an application rate of 200 ppm. Afterdrying, the leaf discs were infested with an aphid population of mixedages. After an incubation period of 7 days, samples were checked formortality.

The following compounds gave at least 80% control of Thrips tabaci: 1,2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19.

Tetranychus urticae (Two-Spotted Spider Mite):

Bean leaf discs on agar in 24-well microtiter plates were sprayed withtest solutions at an application rate of 200 ppm. After drying, the leafdiscs are infested with mite populations of mixed ages. 8 days later,discs are checked for egg mortality, larval mortality, and adultmortality.

The following compounds gave at least 80% control of Tetranychusurticae: 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18,19.

Myzus persicae (Green Peach Aphid):

Sunflower leaf discs were placed on agar in a 24-well microtiter plateand sprayed with test solutions at an application rate of 200 ppm. Afterdrying, the leaf discs were infested with an aphid population of mixedages. After an incubation period of 6 DAT, samples were checked formortality.

The following compounds gave at least 80% control of Myzus persicae: 1,2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19.

The invention claimed is:
 1. A compound according to the formula (IV)

wherein X is hydrogen or F and R¹ is selected from ethyl, n-propyl andn-butyl R is selected from halogen, C₁-C₆-alkyl-C(O)O—, phenyl-C(O)O—,C₁-C₆-alkoxy-C(O)O—, phenoxy-C(O)O—, benzyloxy-C(O)O— and imidazol-1-yl,or a salt thereof.
 2. A method of use of compounds according to theformula (IV)

for the production of compounds according to formula (V)

wherein X is hydrogen or F and R¹ is selected from methyl, ethyl,n-propyl and n-butyl, R is selected from halogen, C₁-C₆-alkyl-C(O)O—,phenyl-C(O)O—, C₁-C₆-alkoxy-C(O)O—, phenoxy-C(O)O—, benzyloxy-C(O)O— andimidazol-1-yl, and Q¹ is 4-pyridyl or 1-oxidopyridin-1-ium-4-yl; or asalt thereof; provided that when R₁ is methyl, than R is not Cl.
 3. Acompound according to the formula (IV)

wherein X is hydrogen or F and R¹ is selected from methyl, ethyl,n-propyl and n-butyl R is selected from F, Br, C₁-C₆-alkyl-C(O)O—,phenyl-C(O)O—, C₁-C₆-alkoxy-C(O)O—, phenoxy-C(O)O—, benzyloxy-C(O)O— andimidazol-1-yl, or a salt thereof.